Acetic Acid → N-Cyclopropylcyclohexanamine

Participants

Reaction Steps

To cyclohexanone (1.0 mL, 10 mmol) in dichloroethane (30 mL) was added cyclopropylamine (0.70 mL, 10 mmol), NaBH(OAc)3 (3.18 g, 15 mmol) and AcOH (0.57 mL, 10 mmol). The reaction was stirred at room temperature for 10 h. The reaction mixture was poured into water (60 mL) and acidified to pH 2 with 5 N HCl followed by removal of the organic portion. The aqueous portion was brought to pH>12 with 5 N NaOH and extracted with CH2Cl2 (3×30 mL). The collected organic extracts were dried with Na2SO4 and the volatile organics were removed in vacuo to afford the desired intermediate.

Provenance & Evidence