4-Allyl-4-ethylmorpholinium chloride

In the title molecular salt, C9H18NO+·Cl−, the morpholine ring adopts a chair conformation. In the crystal structure, intramolecular C—H⋯Cl bonds occur and intermolecular C—H⋯O and C—H⋯Cl hydrogen bonds link the molecules.

In the title molecular salt, C 9 H 18 NO + ÁCl À , the morpholine ring adopts a chair conformation. In the crystal structure, intramolecular C-HÁ Á ÁCl bonds occur and intermolecular C-HÁ Á ÁO and C-HÁ Á ÁCl hydrogen bonds link the molecules.
Experimental Crystal data

Comment
Quaternary morpholine halides are valuable precursors for the preparation of ionic liquids (ILs) by ion metathesis (Kim et al., 2005). The excellent conductivity, broad electrochemical window, thermal stability, and low volatility of ILs have made them promising media for electrochemical processes (Abedin et al., 2004;Abedin et al., 2005). In particular, ILs based on the morpholinium cation are favored because of their low cost, easy synthesis and electrochemical stability (Kim et al., 2006). So far, only a few crystallographic studies have been performed on salts. We report herein the crystal structure of the title compound.
In the crystal structure, intramolecular C-H···Cl and intermolecular C-H···O and C-H···Cl hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure.

Experimental
Under vigorous stirring, allyl chloride (0.1 mol) was added to a solution of 4-ethylmorpholine (0.1 mol) in acetonitrile (20 ml). The mixture was stirred at 333 K for 2 h. The mixture was filtered to remove excess N-ethyl morpholine and allyl chloride and washed with acetone to give the title compound. It was crystallized from ethanol/acetone mixture (1:20) by slow evaporation.

Refinement
H atoms were positioned geometrically, with C-H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl H, respectively, and constrained to ride on their parent atoms with U iso (H) = xU eq (C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms. Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.