Cyclohexylisopropylamine → HCID 19754867, compound

Participants

Reaction Steps

To a stirred, cold (0° C.) solution of 4-bromo-3-chlorobenzoyl chloride (6.14 g, 24.2 mmol) in tetrahydrofuran (20 ml) is added dropwise a solution of isopropyl cyclohexyl amine (6.841g, 48.4 mmol) in THF (7 mL). After stirring for 1 hr. at 0° C., the reaction is stirred at room temperature for 3 hr. and refluxed for 3 hr. The reaction is concentrated in vacuo and the residual mass is dissolved in ethyl ether and water. The layers are separated and the organic layer washed once with water, twice with 0.5N HCl, once more with water, twice with 5% aqueous NaHO3 solution, and once with water. After drying over sodium sulfate, the organic layer is filtered, and the filtrate concentrated in vacuo to give the crude product. This material is purified by chromatography on silica gel using mixtures of EtOAc, and hexane as eluents to give the title compound.

Provenance & Evidence