Reaction #2446079

Reaction equation

Sodium borohydride

1-amino-2-propanol

cyclohexanone

→

1-(cyclohexylamino)propan-2-ol

Solvents

ethanol

Conditions

Workup

1. 1
   workup.STIRRINGstirred at rt for 15 minutes
2. 2
   OtherThe resultant reaction mixture
3. 3
   Otherwas quenched with water
4. 4
   Filtrationfiltered through the Celite® reagent, and solvent
5. 5
   Otherwas evaporated
6. 6
   workup.DISSOLUTIONThe residue was dissolved in 2N HCl
7. 7
   Washwashed with ethyl acetate
8. 8
   ExtractionThe compound was extracted with ethyl acetate
9. 9
   DryingThe organic layer was dried over sodium sulphate
10. 10
    Concentrationconcentrated to dryness

Procedure

To a solution of 1-amino-2-propanol (15 g, 0.199 mol) in ethanol (300 ml) was added cyclohexanone (31.4 mL, 0.299 mol). The reaction mixture was stirred at 0-10° C. for 10 minutes. Sodium borohydride (10.8 g, 0.285 mol) was added at 0° C., then stirred at rt for 15 minutes. The resultant reaction mixture was quenched with water, filtered through the Celite® reagent, and solvent was evaporated. The residue was dissolved in 2N HCl, washed with ethyl acetate; the pH of the aqueous layer was adjusted to 8 using saturated sodium bicarbonate solution. The compound was extracted with ethyl acetate. The organic layer was dried over sodium sulphate, concentrated to dryness, and the crude material was subjected to column chromatography to obtain 1-(cyclohexylamino)propan-2-ol. Yield: 22 g (70.1%); 1H NMR (400 MHz, DMSO-d6) δ 8.25 (bs, 1 H), 5.25 (bs, 1 H), 3.95-3.91 (m, 1 H), 2.89-2.88 (dd, J=6, 9 Hz, 2 H), 2.71-2.66 (m, 1 H), 2.00-1.99 (m, 2 H), 1.75-1.72 (m, 2 H), 1.60-1.57 (m, 1 H), 1.36-0.93 (m, 8 H).

Source