Reaction #2446083

Reaction equation

NaBH4

1-amino-2-propanol

cyclohexanone

→

1-(cyclohexylamino)propan-2-ol

Solvents

ethanol

Conditions

Workup

1. 1
   workup.STIRRINGThe reaction mixture was stirred at rt for 15 minutes
2. 2
   Otherquenched with water
3. 3
   FiltrationThe reaction mixture was filtered through a Celite® pad
4. 4
   Concentrationthe filtrate was concentrated
5. 5
   workup.DISSOLUTIONThe residue was dissolved in DCM
6. 6
   Dryingdried over Na2SO4
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated

Procedure

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.

Source