2-Bromopropane → HCID 13923376, compound

Participants

Reaction Steps

13.5 g (0.1 mole) of 3-methoxyphenylacetonitrile were dissolved in 15 ml of toluene, and 52 g (0.8 mole) of 85% strength potassium hydroxide powder and 0.2 g of tris(3,6-dioxaheptyl)-amine were added. Thereafter, 12.3 g (0.1 mole) of isopropyl bromide were added dropwise to the stirred mixture at a rate such that the reaction temperature did not exceed 50° C. When the addition was complete, stirring was continued for 2 hours at 50° C., after which a solution of 21.2 g (0.1 mole) of N-(3-chloropropyl)-N-methylphenethylamine in 20 ml of toluene was added at 90° C. The reaction mixture was stirred for a further 3 hours at 90° C. and cooled, after which 100 ml of water were added and the toluene phase was separated off. The toluene was distilled off to give a yellow oil, which was chromatographed over a silica gel column using a solvent mixture consisting of 9:1:0.5 methylene chloride/acetone/ methanol. The chromatographically pure base was dissolved in ethyl acetate, and the hydrochloride was precipitated with ethanolic hydrochloric acid. 26.1 g (65%) of a product of melting point 154°-156° C. were obtained.

Provenance & Evidence