N,N-Dimethyl-3-(1-naphth­yloxy)-3-(2-thien­yl)propan-1-amine

Tao, X.; Zhang, X.-Q.; Yuan, L.; Wang, J.-T.

doi:10.1107/S1600536808003255

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Page o553

doi:10.1107/S1600536808003255

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N,N-Dimethyl-3-(1-naphthyloxy)-3-(2-thienyl)propan-1-amine

Xiao Tao,^a Xiao-Qing Zhang,^b Lin Yuan ^a and Jin-Tang Wang ^a ^*

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China, and ^bNanjing Huawei Medicinal Science, Development Co., Ltd., Nanjing 210036, People's Republic of China
^*Correspondence e-mail: wjt@njut.edu.cn

(Received 18 December 2007; accepted 30 January 2008; online 6 February 2008)

The title compound, C₁₉H₂₁NOS, is an intermediate for the synthesis of duloxetine hydrochloride. In the molecular structure, the thiophene and naphthalene ring systems make a dihedral angle of 87.5°. All bond lengths and angles involving heteroatoms are as expected. In the crystal structure, no classical hydrogen bonds are found.

Related literature

For the preparation of duloxetine see: Deeter et al. (1990 ). For related hydroxy derivatives of the title molecule, see: Tao, Bin et al. (2006 ); Tao, Li et al. (2006 ).

Experimental

Crystal data

C₁₉H₂₁NOS
M_r = 311.43
Monoclinic, P 2₁ /n
a = 9.6140 (19) Å
b = 18.578 (4) Å
c = 9.905 (2) Å
β = 104.53 (3)°
V = 1712.5 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 293 (2) K
0.40 × 0.30 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.928, T_max = 0.981
3550 measured reflections
3352 independent reflections
2009 reflections with I > 2s(I)
R_int = 0.038
3 standard reflections every 200 reflections intensity decay: <1%

Refinement

R[F² > 2σ(F²)] = 0.070
wR(F²) = 0.194
S = 1.04
3352 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1981 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808003255/bh2157sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808003255/bh2157Isup2.hkl

checkCIF report

Comment top

The title compound, (I), an is intermediate for Duloxetine hydrochloride (Deeter et al., 1990). The crystal structure determination of (I) has been carried out in order to elucidate its molecular conformation. In the molecular structure (Fig. 1) bond lengths and angles are within normal ranges and compare well with those observed in the corresponding alcohol, 3-hydroxy-N,N-dimethyl-3-(2-thienyl)propanamine (Tao, Bin et al., 2006; Tao, Li et al., 2006). The thiophene (S/C6···C9) and naphthalene (C10···C19) rings are planar and the dihedral angle between them is 87.5°. In the crystal structure, no classic hydrogen bonds are found. It may then be assumed that dipole-dipole and van der Waals interactions are effective for the molecular packing (Fig. 2).

Related literature top

For the preparation of duloxetine see: Deeter et al. (1990). For related hydroxyl derivatives of the title molecule, see: Tao, Bin et al. (2006); Tao, Li et al. (2006).

Experimental top

N,N-Dimethyl-3-(2-thienyl)-3-hydroxylpropanamine (9.25 g, 0.05 mol) was dissolved in 30 ml of dimethylsulfoxide. Sodium hydride (60%, 1.5 g, 0.225 mol) was added to the solution with stirring at room temperature for another 15 min. Then, 1-fluoronaphthalene (8.75 g, 0.06 mol) was added, and the mixture was stirred for 8 h. at 323 K. The mixture was poured into 50 ml of ice water, and the pH was adjusted to 4–5 using acetic acid. 50 ml of hexane was added, stirred and the layers were separated. The aqueous phase was stirred with 30 ml of hexane, the pH was adjusted to 12 using 25% aqueous sodium hydroxide, 30 ml of ethyl acetate was added, stirred and the layers were separated. The aqueous phase was extracted with another 30 ml of ethyl acetate, and the organic extracts were combined, washed with 30 ml of water, dried over magnesium sulfate. The solvent was removed under vacuum to obtain (I) as a brown oil (yield: 11.3 g, 72.9%). The title compound (I) was dissolved in a mixture of ethanol and acetone (2:1). After 14 days, brown single crystals were collected.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1981); cell refinement: CAD-4 Software (Enraf–Nonius, 1981); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of (I). Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The crystal packing of (I) viewed along [100].

N,N-Dimethyl-3-(1-naphthyloxy)-3-(2-thienyl)propan-1-amine top

Crystal data top

C₁₉H₂₁NOS	F(000) = 664
M_r = 311.43	D_x = 1.208 Mg m⁻³
Monoclinic, P2₁/n	Melting point = 386–388 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 9.6140 (19) Å	Cell parameters from 25 reflections
b = 18.578 (4) Å	θ = 10–13°
c = 9.905 (2) Å	µ = 0.19 mm⁻¹
β = 104.53 (3)°	T = 293 K
V = 1712.5 (6) Å³	Block, brown
Z = 4	0.40 × 0.30 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	2009 reflections with I > 2s(I)
Radiation source: fine-focus sealed tube	R_int = 0.038
Graphite monochromator	θ_max = 26.0°, θ_min = 2.4°
ω/2θ scans	h = 0→11
Absorption correction: ψ scan (North et al., 1968)	k = 0→22
T_min = 0.928, T_max = 0.981	l = −12→11
3550 measured reflections	3 standard reflections every 200 reflections
3352 independent reflections	intensity decay: <1%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.194	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.08P)² + 0.85P] where P = (F_o² + 2F_c²)/3
3352 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₉H₂₁NOS	V = 1712.5 (6) Å³
M_r = 311.43	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.6140 (19) Å	µ = 0.19 mm⁻¹
b = 18.578 (4) Å	T = 293 K
c = 9.905 (2) Å	0.40 × 0.30 × 0.10 mm
β = 104.53 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2009 reflections with I > 2s(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.038
T_min = 0.928, T_max = 0.981	3 standard reflections every 200 reflections
3550 measured reflections	intensity decay: <1%
3352 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.070	0 restraints
wR(F²) = 0.194	H-atom parameters constrained
S = 1.04	Δρ_max = 0.45 e Å⁻³
3352 reflections	Δρ_min = −0.32 e Å⁻³
199 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S	0.03342 (12)	0.25309 (6)	0.17997 (10)	0.0561 (3)
O	0.1693 (2)	0.34125 (12)	0.0007 (2)	0.0445 (6)
N	−0.1370 (3)	0.47356 (16)	−0.2560 (3)	0.0517 (8)
C1	−0.2401 (5)	0.4470 (2)	−0.3807 (5)	0.0777 (14)
H1A	−0.2777	0.4015	−0.3607	0.117*
H1B	−0.1929	0.4412	−0.4547	0.117*
H1C	−0.3173	0.4809	−0.4086	0.117*
C2	−0.0803 (5)	0.5421 (2)	−0.2843 (5)	0.0753 (13)
H2A	−0.0133	0.5593	−0.2016	0.113*
H2B	−0.1575	0.5760	−0.3123	0.113*
H2C	−0.0322	0.5367	−0.3577	0.113*
C3	−0.0227 (4)	0.4218 (2)	−0.2029 (4)	0.0517 (10)
H3A	0.0559	0.4461	−0.1383	0.062*
H3B	0.0131	0.4041	−0.2800	0.062*
C4	−0.0708 (4)	0.3584 (2)	−0.1295 (4)	0.0506 (10)
H4A	−0.1016	0.3758	−0.0493	0.061*
H4B	−0.1527	0.3357	−0.1924	0.061*
C5	0.0463 (4)	0.30309 (19)	−0.0816 (4)	0.0439 (9)
H5A	0.0711	0.2822	−0.1634	0.053*
C6	0.0029 (4)	0.24339 (18)	0.0033 (4)	0.0406 (8)
C7	−0.0719 (4)	0.17959 (18)	−0.0465 (4)	0.043
H7A	−0.0997	0.1649	−0.1392	0.052*
C8	−0.0976 (4)	0.1414 (2)	0.0708 (4)	0.0542 (10)
H8A	−0.1447	0.0973	0.0620	0.065*
C9	−0.0482 (4)	0.1743 (2)	0.1943 (4)	0.0510 (10)
H9A	−0.0580	0.1556	0.2785	0.061*
C10	0.3039 (4)	0.31259 (19)	0.0180 (3)	0.0403 (8)
C11	0.3328 (4)	0.2446 (2)	−0.0182 (4)	0.0498 (9)
H11A	0.2584	0.2131	−0.0572	0.060*
C12	0.4781 (5)	0.2225 (2)	0.0045 (4)	0.0574 (11)
H12A	0.4982	0.1762	−0.0211	0.069*
C13	0.5882 (5)	0.2673 (2)	0.0627 (4)	0.0603 (11)
H13A	0.6825	0.2515	0.0761	0.072*
C14	0.5612 (4)	0.3372 (2)	0.1027 (4)	0.0496 (10)
C15	0.6714 (4)	0.3854 (3)	0.1646 (4)	0.0677 (13)
H15A	0.7665	0.3704	0.1814	0.081*
C16	0.6431 (5)	0.4528 (3)	0.2002 (5)	0.0746 (13)
H16A	0.7185	0.4836	0.2397	0.089*
C17	0.5021 (5)	0.4765 (2)	0.1781 (4)	0.0655 (12)
H17A	0.4837	0.5230	0.2040	0.079*
C18	0.3900 (4)	0.4320 (2)	0.1186 (4)	0.0481 (9)
H18A	0.2961	0.4485	0.1038	0.058*
C19	0.4161 (4)	0.36147 (19)	0.0798 (3)	0.0409 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0651 (7)	0.0585 (6)	0.0425 (5)	−0.0028 (5)	0.0094 (5)	−0.0023 (5)
O	0.0335 (13)	0.0410 (14)	0.0566 (15)	−0.0007 (11)	0.0070 (11)	−0.0068 (11)
N	0.0482 (19)	0.0464 (18)	0.058 (2)	0.0008 (15)	0.0083 (15)	0.0088 (15)
C1	0.065 (3)	0.070 (3)	0.081 (3)	−0.003 (2)	−0.011 (2)	0.018 (3)
C2	0.074 (3)	0.054 (3)	0.095 (4)	−0.003 (2)	0.017 (3)	0.013 (3)
C3	0.041 (2)	0.055 (2)	0.057 (2)	−0.0018 (18)	0.0077 (18)	0.0090 (19)
C4	0.040 (2)	0.055 (2)	0.053 (2)	0.0009 (18)	0.0033 (17)	0.0086 (19)
C5	0.044 (2)	0.045 (2)	0.0414 (19)	−0.0021 (17)	0.0088 (16)	−0.0027 (16)
C6	0.0393 (19)	0.044 (2)	0.0367 (17)	0.0071 (16)	0.0068 (14)	0.0008 (16)
C7	0.043	0.043	0.043	0.000	0.011	0.000
C8	0.060 (3)	0.041 (2)	0.059 (3)	−0.0030 (19)	0.012 (2)	−0.0004 (19)
C9	0.062 (3)	0.047 (2)	0.046 (2)	0.0077 (19)	0.0170 (19)	0.0069 (18)
C10	0.0380 (19)	0.048 (2)	0.0372 (19)	0.0080 (16)	0.0127 (15)	0.0072 (16)
C11	0.055 (2)	0.050 (2)	0.048 (2)	0.0039 (19)	0.0182 (18)	0.0050 (19)
C12	0.069 (3)	0.056 (2)	0.055 (2)	0.022 (2)	0.029 (2)	0.011 (2)
C13	0.050 (2)	0.084 (3)	0.049 (2)	0.025 (2)	0.0167 (19)	0.016 (2)
C14	0.041 (2)	0.070 (3)	0.039 (2)	0.0091 (19)	0.0118 (17)	0.0115 (19)
C15	0.039 (2)	0.103 (4)	0.059 (3)	−0.002 (2)	0.008 (2)	0.005 (3)
C16	0.051 (3)	0.101 (4)	0.067 (3)	−0.019 (3)	0.004 (2)	−0.007 (3)
C17	0.064 (3)	0.060 (3)	0.069 (3)	−0.009 (2)	0.011 (2)	−0.010 (2)
C18	0.046 (2)	0.052 (2)	0.046 (2)	−0.0025 (18)	0.0120 (17)	0.0017 (18)
C19	0.0399 (19)	0.050 (2)	0.0324 (18)	0.0023 (17)	0.0085 (15)	0.0062 (16)

Geometric parameters (Å, º) top

S—C6	1.709 (3)	C7—H7A	0.9300
S—C9	1.683 (4)	C8—C9	1.343 (5)
O—C10	1.370 (4)	C8—H8A	0.9300
O—C5	1.443 (4)	C9—H9A	0.9300
N—C2	1.440 (5)	C10—C11	1.360 (5)
N—C3	1.455 (5)	C10—C19	1.425 (5)
N—C1	1.462 (5)	C11—C12	1.419 (5)
C1—H1A	0.9600	C11—H11A	0.9300
C1—H1B	0.9600	C12—C13	1.357 (6)
C1—H1C	0.9600	C12—H12A	0.9300
C2—H2A	0.9600	C13—C14	1.400 (5)
C2—H2B	0.9600	C13—H13A	0.9300
C2—H2C	0.9600	C14—C15	1.406 (6)
C3—C4	1.517 (5)	C14—C19	1.429 (5)
C3—H3A	0.9700	C15—C16	1.345 (6)
C3—H3B	0.9700	C15—H15A	0.9300
C4—C5	1.511 (5)	C16—C17	1.390 (6)
C4—H4A	0.9700	C16—H16A	0.9300
C4—H4B	0.9700	C17—C18	1.369 (5)
C5—C6	1.513 (5)	C17—H17A	0.9300
C5—H5A	0.9800	C18—C19	1.405 (5)
C6—C7	1.410 (5)	C18—H18A	0.9300
C7—C8	1.435 (5)

C9—S—C6	91.74 (18)	C6—C7—H7A	126.0
C10—O—C5	119.6 (3)	C8—C7—H7A	126.0
C2—N—C3	111.4 (3)	C9—C8—C7	114.8 (3)
C2—N—C1	110.1 (3)	C9—C8—H8A	122.6
C3—N—C1	111.9 (3)	C7—C8—H8A	122.6
N—C1—H1A	109.5	C8—C9—S	112.6 (3)
N—C1—H1B	109.5	C8—C9—H9A	123.7
H1A—C1—H1B	109.5	S—C9—H9A	123.7
N—C1—H1C	109.5	C11—C10—O	125.2 (3)
H1A—C1—H1C	109.5	C11—C10—C19	121.4 (3)
H1B—C1—H1C	109.5	O—C10—C19	113.3 (3)
N—C2—H2A	109.5	C10—C11—C12	119.1 (4)
N—C2—H2B	109.5	C10—C11—H11A	120.5
H2A—C2—H2B	109.5	C12—C11—H11A	120.5
N—C2—H2C	109.5	C13—C12—C11	121.4 (4)
H2A—C2—H2C	109.5	C13—C12—H12A	119.3
H2B—C2—H2C	109.5	C11—C12—H12A	119.3
N—C3—C4	113.1 (3)	C12—C13—C14	120.6 (4)
N—C3—H3A	109.0	C12—C13—H13A	119.7
C4—C3—H3A	109.0	C14—C13—H13A	119.7
N—C3—H3B	109.0	C13—C14—C15	122.7 (4)
C4—C3—H3B	109.0	C13—C14—C19	119.4 (4)
H3A—C3—H3B	107.8	C15—C14—C19	117.8 (4)
C5—C4—C3	112.7 (3)	C16—C15—C14	121.8 (4)
C5—C4—H4A	109.1	C16—C15—H15A	119.1
C3—C4—H4A	109.1	C14—C15—H15A	119.1
C5—C4—H4B	109.1	C15—C16—C17	120.5 (4)
C3—C4—H4B	109.1	C15—C16—H16A	119.8
H4A—C4—H4B	107.8	C17—C16—H16A	119.8
O—C5—C4	106.5 (3)	C18—C17—C16	120.5 (4)
O—C5—C6	110.3 (3)	C18—C17—H17A	119.8
C4—C5—C6	112.7 (3)	C16—C17—H17A	119.8
O—C5—H5A	109.1	C17—C18—C19	120.4 (4)
C4—C5—H5A	109.1	C17—C18—H18A	119.8
C6—C5—H5A	109.1	C19—C18—H18A	119.8
C7—C6—C5	127.5 (3)	C18—C19—C10	122.9 (3)
C7—C6—S	112.9 (3)	C18—C19—C14	119.0 (3)
C5—C6—S	119.4 (3)	C10—C19—C14	118.1 (3)
C6—C7—C8	108.0 (3)

C2—N—C3—C4	161.7 (4)	C19—C10—C11—C12	−0.9 (5)
C1—N—C3—C4	−74.6 (4)	C10—C11—C12—C13	0.7 (6)
N—C3—C4—C5	176.9 (3)	C11—C12—C13—C14	0.2 (6)
C10—O—C5—C4	−157.5 (3)	C12—C13—C14—C15	179.4 (4)
C10—O—C5—C6	80.0 (4)	C12—C13—C14—C19	−1.0 (6)
C3—C4—C5—O	53.6 (4)	C13—C14—C15—C16	178.9 (4)
C3—C4—C5—C6	174.6 (3)	C19—C14—C15—C16	−0.8 (6)
O—C5—C6—C7	−154.8 (3)	C14—C15—C16—C17	0.9 (7)
C4—C5—C6—C7	86.3 (4)	C15—C16—C17—C18	−0.7 (7)
O—C5—C6—S	30.0 (4)	C16—C17—C18—C19	0.4 (6)
C4—C5—C6—S	−88.8 (3)	C17—C18—C19—C10	179.7 (3)
C9—S—C6—C7	0.6 (3)	C17—C18—C19—C14	−0.3 (5)
C9—S—C6—C5	176.4 (3)	C11—C10—C19—C18	−179.9 (3)
C5—C6—C7—C8	−176.3 (3)	O—C10—C19—C18	−0.1 (5)
S—C6—C7—C8	−0.8 (4)	C11—C10—C19—C14	0.2 (5)
C6—C7—C8—C9	0.7 (5)	O—C10—C19—C14	180.0 (3)
C7—C8—C9—S	−0.3 (4)	C13—C14—C19—C18	−179.2 (3)
C6—S—C9—C8	−0.2 (3)	C15—C14—C19—C18	0.5 (5)
C5—O—C10—C11	−10.8 (5)	C13—C14—C19—C10	0.8 (5)
C5—O—C10—C19	169.4 (3)	C15—C14—C19—C10	−179.6 (3)
O—C10—C11—C12	179.3 (3)

Experimental details

Crystal data
Chemical formula	C₁₉H₂₁NOS
M_r	311.43
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	9.6140 (19), 18.578 (4), 9.905 (2)
β (°)	104.53 (3)
V (Å³)	1712.5 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.40 × 0.30 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.928, 0.981
No. of measured, independent and observed [I > 2s(I)] reflections	3550, 3352, 2009
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.070, 0.194, 1.04
No. of reflections	3352
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.32

Computer programs: CAD-4 Software (Enraf–Nonius, 1981), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

S—C6	1.709 (3)	N—C2	1.440 (5)
S—C9	1.683 (4)	N—C3	1.455 (5)
O—C10	1.370 (4)	N—C1	1.462 (5)
O—C5	1.443 (4)

C9—S—C6	91.74 (18)	O—C5—C6	110.3 (3)
C10—O—C5	119.6 (3)	C7—C6—S	112.9 (3)
C2—N—C3	111.4 (3)	C5—C6—S	119.4 (3)
C2—N—C1	110.1 (3)	C8—C9—S	112.6 (3)
C3—N—C1	111.9 (3)	C11—C10—O	125.2 (3)
N—C3—C4	113.1 (3)	O—C10—C19	113.3 (3)
O—C5—C4	106.5 (3)

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

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