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

Temperature

0 °C

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, 1 H), 3.61-3.57 (m, 1 H), 2.47-2.30 (m, 3 H), 1.78-1.75 (m, 2 H), 1.66-1.63 (m, 2 H), 1.55-1.52 (m, 1 H), 1.23-1.12 (m, 3 H), 1.03-0.89 (m, 5 H). 1-(cyclohexylamino)propan-2-ol may also be prepared by following procedure of Example 1.

1. stirringThe reaction mixture was stirred at rt for 15 minutes
2. customquenched with water
3. filtrationThe reaction mixture was filtered through a Celite® pad
4. concentrationthe filtrate was concentrated
5. dissolutionThe residue was dissolved in DCM
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-8db7f6189676475c8a82170d539aecd7

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08685418B2