Methylamine → HCID 178484783, compound

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Reaction Steps

26 g (0.15 mol) of 4-phenylcyclohexanone are stirred with 160 ml of a 6 % methylamine solution in toluene in the presence of 30 g of molecular sieve M 3 Å overnight in a sealed flask. After filtering and concentration by evaporation the residue is dissolved in 200 ml of methanol and at −20° C. 7.8 g sodium borohydride are added batchwise. After it has all been added the mixture is stirred overnight at ambient temperature. After evaporation of the methanol the remainder is taken up in 150 ml of ice water and made strongly acidic with conc. hydrochloric acid. After saturation with common salt the hydrochloride precipitated is suction filtered, the mother liquor is made strongly alkaline with 6N sodium hydroxide solution, extracted with ethyl acetate, dried and evaporated down. The hydrochloride precipitated is suspended in a mixture of water and ethyl acetate and, under cooling, made strongly alkaline with 6N sodium hydroxide solution. The ethyl acetate phase is washed with water and saturated saline solution, dried and evaporated down. Crystallisation of the residue from petroleum ether yields 15.1 g trans-N-methyl-4-phenylcyclohexylamine (colourless crystals). The petroleum ether mother liquor is evaporated down and combined with the evaporation residue from the hydrochloride precipitation. Separation on aluminium oxide (activity stage III, ethyl acetate/petroleum ether=1:1 to 2:1, v:v) yields 2.4 g cis-N-methyl-4-phenylcyclohexylamine,

Provenance & Evidence