Dichloromethane → HCID 178483392, compound

Participants

Reaction Steps

To a stirred solution of trans-4-[4-(4-phenylcyclohexylamino)-butyl]phenol (370 mg, 1.1 mmol) in a mixture of MeOH (5 mL) H2O (0.5 mL), and CH2Cl2 (5 mL) was added ρformaldehyde (170 mg, 5.7 mmol). After stirring for 10 minutes, NaBH(OAc)3 (300 mg, 1.4 mmol) was added, and the reaction mixture was stirred for 12 hours. Solid NaOH was added to give a clear solution, which was then concentrated under reduced pressure. Purification by flash chromatography (silica, 89:10:1 CH2Cl2:MeOH:NH4OH) and formation of the HCl salt gave (b) trans-4-{4-[methyl-(4-phenylcyclohexyl)amino]butyl}-phenol (230 mg, 56%), as a white solid: mp 234-236° C.; IR (KBr): 2942, 1613, 1515 cm−1; 1H NMR (500 MHz, DMSO-d6) δ 9.96 (br s, 1H), 9.13 (s, 1H), 7.31-7.18 (m, 5H), 7.00 (d, J=8.5 Hz, 2H), 6.68(d, J=8.5 Hz, 2H), 3.33-3.23 (m, 1H), 3.17-3.09 (m, 1H), 3.02-2.95 (m, 1H), 2.67(d, J=5 Hz, 3H), 2.55-2.49 (m, 3H), 2.16-2.06 (m, 2H), 1.95-1.89 (m, 2H), 1.72-1.50 (m, 8H); CI—MS (methane) (m/z): 338 [M+H]+; HPLC: method A, 6.38 minutes (>99%); method B, 11.28 minutes (>99%); Anal. Calcd for C23H31NO.HCl: C, 73.87; H, 8.62; N, 3.75. Found: C, 73.61; H, 8.55; N, 3.66.

Provenance & Evidence