반응 #436393

반응 방정식

aniline

1-azabicyclo[2.2.2]octan-3-one hydrochloride

Na(OAc)3BH

→

N-Phenyl-1-azabicyclo[2.2.2]octan-3-amine

수율 30.0%

용매

dichloroethane

반응 조건

후처리

1. 1
   기타The reaction was quenched with 3 N NaOH
2. 2
   기타The layers were separated
3. 3
   추출the aqueous layer was extracted with an additional portion of CHCl3
4. 4
   건조dried over NaSO4
5. 5
   여과filtered
6. 6
   기타the solvent was evaporated in vacuo
7. 7
   기타Th residue was chromatographed on silica (95/5 CHCl3/10% NH4OH in MeOH)

실험 절차

(Method 1A) To a mixture of 9.3 g (0.1 mol) of aniline and 16.1 g (0.1 mol) of 1-azabicyclo[2.2.2]octan-3-one hydrochloride in 250 mL of dichloroethane (DCE) was added 31.8 g (0.15 mol) of Na(OAc)3BH and the mixture was stirred overnight at room temperature. The reaction was quenched with 3 N NaOH. The layers were separated and the aqueous layer was extracted with an additional portion of CHCl3. The organic layers were combined, dried over NaSO4, and then filtered and the solvent was evaporated in vacuo. Th residue was chromatographed on silica (95/5 CHCl3/10% NH4OH in MeOH) to give N-Phenyl-1-azabicyclo[2.2.2]octan-3-amine (6.0 g 30%) as an off-white solid. MH+=203. 1H NMR (CDCl3) 1.46 (m, 1H), 1.75 (m, 3H), 2.0 (m, 1H), 2.55 (m, 1H), 2.95 (m, 4H), 3.4 (m, 2H), 3.8 (s, 1H), 6.6 (d, 2H), 6.75 (t, 1H), 7.2 (t, 2H).

출처