تفاعل #2446079

معادلة التفاعل

Sodium borohydride

1-amino-2-propanol

cyclohexanone

→

1-(cyclohexylamino)propan-2-ol

المذيبات

ethanol

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGstirred at rt for 15 minutes
2. 2
   أخرىThe resultant reaction mixture
3. 3
   أخرىwas quenched with water
4. 4
   ترشيحfiltered through the Celite® reagent, and solvent
5. 5
   أخرىwas evaporated
6. 6
   workup.DISSOLUTIONThe residue was dissolved in 2N HCl
7. 7
   غسيلwashed with ethyl acetate
8. 8
   استخلاصThe compound was extracted with ethyl acetate
9. 9
   تجفيفThe organic layer was dried over sodium sulphate
10. 10
    تركيزconcentrated to dryness

الإجراء التجريبي

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).

المصدر