Acetic Acid → 4-methyl-N-(3-methylbutyl)cyclohexan-1-amine

Participants

Reaction Steps

4-trans-methyl-cyclohexylamine hydrochloride (15 g, 100 mmol) in THF-MeOH (2:1, 200 mL) was added solid NaOH (6.01 g, 150 mmol). The mixture was stirred for 30 m before isovaleraldehyde (10.4 g, 120 mmol), 20 mL AcOH was added. Subsequently sodium cyanoborohydride (6.0 g, 150 mmol) was added in small portions. The reaction mixture was stirred for 18 h before H2O (200 mL) was added and the mixture was extracted with DCM (2×100 mL). The organic fraction were dried (MgSO4) before an excess of HCl in diethyl ether were added. The solvent were removed in vacuo and diethyl ether was added (200 mL). The precipitate was filtered off washed with diethyl ether and dried in vacuo to give 18.8 g of (3-methyl-butyl)-(4-methyl-cyclohexyl)-amine.

Provenance & Evidence