Hydrochloric Acid → [1-(4-Chlorophenyl)cyclobutyl](1-methylpyrazol-5-yl)methylamine hydrochloride

Participants

Reaction Steps

1-Methylpyrazole (4.8 g) was added to a mixture of dry ether (60 ml) and a 1.7M solution of butyllithium in hexane (30 ml) under nitrogen at a temperature of less than 5° C. N,N,N'N'-Tetramethylethylenediamine (TMEDA) (8.3 g) was added and the mixture stirred at 0°-5° C. for one and three quarter hours and then 1-(4-chlorophenyl)cyclobutanecarbonitrile (6.0 g) was added and the mixture stirred for 90 minutes at a temperature in the range 0 to 5° C. Water was added and the reaction mixture extracted with ether. The extract was washed, dried and evaporated to give an oil which is [1-(4-chlorophenyl)cyclobutyl](1-methylpyrazol-5yl)methanimine. The imine was stirred with a mixture of sodium borohydride (2 g) in diethyleneglycoldimethyl ether (100 ml) under nitrogen at 95° C. for two hours. The mixture was poured into water and extracted with ether. The extract was washed, dried and evaporated to give a residue which was dissolved in dry ether. Hydrogen chloride gas was passed through the ethereal solution to give a hydrochloride salt of [1-(4-chlorophenyl)cyclobutyl](1-methylpyrazol-5-yl)methylamine hydrochloride (m.p. 316°-318° C.) containing 1.25 moles of hydrochloride and 0.25 moles of water.

Provenance & Evidence