Toluene → 1-Benzyl-4-hydroxy-4-(1,4-benzodioxan-5-yl)piperidine

HRID 963257

반응식

HRID 963257 반응식
C1(C)C=CC=CC=1.Br[C:9]1[C:18]2[O:17][CH2:16][CH2:15][O:14][C:13]=2[CH:12]=[CH:11][CH:10]=1.C([Li])CCC.[CH2:24]([N:31]1[CH2:36][CH2:35][C:34](=[O:37])[CH2:33][CH2:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O>[CH2:24]([N:31]1[CH2:36][CH2:35][C:34]([OH:37])([C:9]2[C:18]3[O:17][CH2:16][CH2:15][O:14][C:13]=3[CH:12]=[CH:11][CH:10]=2)[CH2:33][CH2:32]1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

참가 물질

6

반응물 4

HCID 1140Toluene2회HCID 192201-Benzyl-4-piperidoneHCID 187872685-Bromo-2,3-dihydro-1,4-benzodioxineHCID 178418339Butyllithium

생성물 1

HCID 190820021-Benzyl-4-hydroxy-4-(1,4-benzodioxan-5-yl)piperidine

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A toluene solution (10 ml) of 5-bromo-2,3-dihydrobenzo[1,4]dioxin (10 mmol) was stirred under argon at 0° C. and was treated with the dropwise addition of n-butyllithium (10 mmol) over ten minutes. After stirring for a further twenty minutes a solution of 1-benzyl-4-piperidone in toluene (10 mmol in 10 ml) was added dropwise over five minutes. Stirring was continued for two hours, at which point water (100 ml) was added and the product extracted into ethyl acetate (4×50 ml). The combined organics were washed with water (2×50 ml), brine (75 ml) and dried (MgSO4). Filtration and concentration in vacuo gave an oil.

후처리

  1. additionwas added dropwise over five minutes
  2. additionwas added
  3. extractionthe product extracted into ethyl acetate (4×50 ml)
  4. washThe combined organics were washed with water (2×50 ml), brine (75 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationFiltration and concentration in vacuo
  7. customgave an oil

출처 및 근거

ORD 기록
ord-3739f71d30514f818eec72796ec5874e
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05763460

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