Water → HCID 178463899, compound

Participants

Reaction Steps

To a mixture of LiAlH4 (74 mg, 1.95 mmol) and THF (10 ml) at 0° under Argon, a solution of trans-N-[4-(4-benzyloxy-phenyl)-cyclohexyl]-N-(3-phenyl-propyl)-acetamide (0.43 g, 0.97 mmol) in THF (10 ml) was added. The suspension was stirred for 2 h at RT and for 1 h at reflux. After cooling to 0°, H2O (0.4 ml) was carefully added, followed by 15% NaOH (0.4 ml) and H2O (0.4 ml). The precipitate was removed by filtration and the filtrate dried over Na2SO4, and evaporated. The residue was purified by chromatography over SiO2 (Merck 230-400 mesh) eluting with CH2Cl2—MeOH 95:5 to give trans-[4-(4-benzyloxy-phenyl)-cyclohexyl]-ethyl-(3-phenyl-propyl)-amine (0.11 g, 26%) as a colorless oil. MS: m/e=328.5 (M+H+).

Provenance & Evidence