Benzyl Bromide → trans-4-(Dibenzylamino)cyclohexanol

Participants

Reaction Steps

To a mixture of 4-aminocyclohexanol (3.51 g, 23.15 mmol) and K2CO3 (12.80 g, 93 mmol) in acetonitrile (100 mL) was added benzylbromide (5.64 mL, 47.5 mmol) and the mixture was stirred at reflux for 17 hr. The crude mixture was concentrated in vacuo and the resulting residue was dissolved in water and EtOAc. The separated aqueous layer was extracted with EtOAc (2ט100 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered off and concentrated in vacuo providing crude 4-(dibenzylamino)cyclohexanol as a viscous oil, which was directly used in the next step without further purification. Yield: 6.12 g. LCMS (m/z): 296.1 [M+H]+; Retention time=0.59 min.

Provenance & Evidence