Acetaldehyde → HCID 178464514, compound

Participants

Reaction Steps

Coupling of 6-{trans-4-[(S)-1-methyl-3-phenylpropylamino]cyclohexyl}-3H-benzoxazol-2-one (196 mg, 0.538 mmol) and acetaldehyde (24 mg, 0.538 mmol) following the procedure described in Example 24, followed by formation of the HCl salt, gave 6-(trans-4-{ethyl-[(S)-1-methyl-3-phenylpropyl]-amino}cyclohexyl)-3H-benzoxazol-2-one (110 mg, 50%), as a pale yellow solid (a mixture of diastereomers): mp 221-246° C.; IR (KBr): 3424, 2929, 1771, 1495 cm−1; 1H NMR (500 MHz, DMSO-d6): δ 11.52 (s, 2H), 9.11 (s, 2H), 7.35-7.21 (m, 10H), 7.18 (m, 4H), 7.00 (s, 2H), 3.20 (m, 2H), 2.81 (m, 2H), 2.54 (m, 2H), 2.20-1.51 (m, 28H), 1.44 (d, J=7 Hz, 3H), 1.32 (d, J=7 Hz, 3H), 126 (m, 6H); API-MS (methane) (m/z): 393 [M+H]+; HPLC: method C, 5.88 minutes (97.4%), method D, 11.32 minutes (>99%); Anal. Calcd for C25H32N2O2.HCl.H2O: C, 67.17; H, 7.89; N, 6.27. Found: C, 67.18; H, 7.69; N, 5.98.

Provenance & Evidence