Methylamine → HCID 68673625, compound

Participants

Reaction Steps

A solution of 1-(3-chlorophenyl)cyclohexane-carbaldehyde (119 mg, 0.53 mmol), methyl amine (291 μL, 0.58 mmol, 2.0 M in THF) and sodium cyanoborohydride (100 mg, 1.59 mmol) in 1:1 MeOH:Triethylorthoformate (4 mL) was shaken at RT overnight. The solution was poured into saturated aqueous K2CO3 and washed with EtOAc (2×20 mL). The combined organic washes were dried (Na2SO4), filtered and concentrated. The crude material was dissolved in Et2O and HCl (1.5 mL, 2.0 M in Et2O) was added. The reaction was concentrated and the HCl salt was recrystallized from CH3CN (4.5 mL) to give pure (1-(3-chlorophenyl)cyclohexyl)-N-methylmethanamine hydrochloride as colorless crystals HPLC Rt=8.25 min; 1H NMR (400 mHz, MeOH-d4) 7.43-7.28 (m, 4H) 3.12 (s, 2H), 2.54 (s, 3H), 2.19-2.16 (m, 2H), 1.67-1.30 (m, 8H); LC-MS 7.29 min, (M+1)− 238 @ 7.50 min.

Provenance & Evidence