Aluminium lithium hydride → HCID 178463898, compound

Participants

Reaction Steps

To a stirred solution of trans-N-[4-(4-hydroxyphenyl)cyclohexyl]-N-(3-phenylpropyl)acetamide (282 mg, 0.80 mmol) in anhydrous THF (5 mL) was added LiAlH4 (1.2 mL of a 1M solution in Et2O, 1.2 mmol). After 18 hours, the reaction was quenched by addition of a mixture of H2O (2 mL), 2N NaOH (4 mL), and saturated NaCl (2 mL). The resulting mixture was diluted with Et2O (100 mL) and the resulting mixture was filtered. The filtrate was dried (Na2SO4) and concentrated under reduced pressure. Purification by flash chromatography (90:9:1 CH2Cl2:MeOH:NH4OH) gave trans-4-{4-[N-ethyl-N-(3-phenylpropyl)-amino]cyclohexyl}phenol (130 mg, 48%) as a white solid: mp 192-194° C.; IR (KBr): 3197, 2939, 1614, 1516 cm−1; 1H NMR (500 MHz, DMSO-d6) δ 9.16 (br s, 1H), 7.35-7.23 (m, 5H), 7.02 (d, J=8 Hz, 2H), 6.70 (d, J=8 Hz, 2H), 3.35-3.12 (m, 5H), 2.68 (q, J=5, 2 Hz, 2H), 2.42 (tt, J=9, 2 Hz, 1H), 2.12 (br d, J=9 Hz, 2H), 2.10 (m, 2H), 1.87 (br d, J=9 Hz, 2H), 1.63 (dddd, J=9, 9, 9, 2 Hz, 2H), 1.53 (dddd, J=9, 9, 9, 2 Hz, 2H), 1.27 (t, J=5 Hz, 3H); CI-MS (methane) (m/z): 338 [M+H]+; HPLC: method A, 8.80 minutes (97.8%); method B, 10.66 minutes (99.9%); Anal. Calcd for C23H31NO.HCl.0.125H2O: C, 73.43; H, 8.64; N, 3.72. Found: C, 73.36; H, 8.75; N, 3.56.

Provenance & Evidence