1-Amino-2-propanol → 2-Propanol, 1-(cyclohexylamino)-

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1-amino-2-propanol (1.0 mL, 13.31 mmol) in ethanol (15 mL) was added cyclohexanone (1.9 g, 19.9 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 15 minutes and then NaBH4 (0.725 g, 19.17 mmol) was added. The reaction mixture was stirred at rt for 15 minutes and then quenched with water. The reaction mixture was filtered through a Celite® pad and the filtrate was concentrated. The residue was dissolved in DCM, dried over Na2SO4, filtered and concentrated to provide 1-(cyclohexylamino)propan-2-ol. Yield: 2.6 g (crude). 1H NMR (DMSO-d6) δ 4.39-4.36 (m, 1H), 3.61-3.57 (m, 1H), 2.47-2.30 (m, 3H), 1.78-1.75 (m, 2H), 1.66-1.63 (m, 2H), 1.55-1.52 (m, 1H), 1.23-1.12 (m, 3H), 1.03-0.89 (m, 5H). 1-(cyclohexylamino)propan-2-ol may also be prepared by following procedure of Example 1.

Provenance & Evidence