Dichloromethane → HCID 178483270, compound

Participants

Reaction Steps

To a stirred solution of trans-4-[2-(4-phenylcyclohexylamino)ethyl]phenol (380 mg, 1.3 mmol) in MeOH (5 mL), H2O (0.5 mL), and CH2Cl2 (5 mL) was added ρformaldehyde (200 mg, 6.5 mmol). After stirring for 15 minutes NaBH(OAc)3 (340 mg, 1.6 mmol) was added, and the reaction mixture was stirred for 12 hours. Additional NaBH(OAc)3 (138 mg, 0.65 mmol) was added, and the mixture was stirred for 2 days. NaBH(OAc)3 (138 mg, 0.65 mmol) was added, and stirring was continued for 6 hours. Solid NaOH was added to give a clear solution, which was concentrated under reduced pressure. Purification by flash chromatography (silica, 89:10:1 CH2Cl2:MeOH:NH4OH) and formation of the HCl salt gave trans-4-{2-[methyl(4-phenylcyclohexyl)amino]ethyl}phenol (380 mg, 64%), as an off-white solid: mp 97-105° C.; IR (KBr): 2941, 1614, 1517 cm−1; 1H NMR (500 MHz, DMSO-d6) δ 11.05 (s, 1H), 9.42 (s, 1H), 7.35-7.15 (m, 5H), 7.10 (br d, J=8 Hz, 2H), 6.77 (br d, J=8 Hz, 2H), 3.49-2.94 (m, 6H), 2.80-2.70 (m, 2H), 2.56-2.48 (m, 1H), 2.30-2.11 (m, 2H), 1.89 (br d, J=11.5 Hz, 2H), 1.75-1.50 (m, 4H); CI—MS (methane) (m/z): 310 [M+H]+; HPLC: method A, 5.99 minutes (99.4%); method B, 10.68 minutes (99.1%); Anal. Calcd for C21H27NO.HCl.0.25H2O: C, 71.98; H, 8.20; N, 4.00. Found: C, 71.60; H, 8.31; N, 3.86.

Provenance & Evidence