Methylamine → HCID 178484783, compound

Participants

Reaction Steps

Methylamine (5.7 mL of a 2.0 M in THF, 11.4 mmol) was added to a solution of 4-phenylcyclohexanone 1 (2.0 g, 11 mmol) in anhydrous THF (30 mL), and the mixture was stirred at room temperature for 4 hours. BH3—SMe2 1.6 mL, 16 mmol) was added, and stirring was continued overnight. After quenching the reaction with MeOH, the solvents were removed under reduced pressure. The crude solid was dissolved in MeOH (10 mL), HCl (15 mL of a 1.0 M solution in Et2O, 15 mmol) was added, and the mixture concentrated under reduced pressure. Purification by flash chromatography (silica, 9:1:0.1 CH2Cl2: MeOH:NH4OH) gave trans-1-(methylamino)-4-phenylcyclohexane 6 (0.80 g, 39%) as a white solid: 1H NMR (300 MHz, CD3 OD) δ 7.27-7.11 (m, 5H), 2.64 m, 1H), 2.51 (obs m, 1H), 2.48 (s, 3H), 2.47 (s, 3H), 2.11 (br d, J=11 Hz, 2H), 1.93 (br d, J=11 Hz, 2H), 1.59 (dddd, J=11, 11, 2, 2 Hz, 2H), 1.42 (dddd, J=11, 11, 2, 2 Hz, 2H).

Provenance & Evidence