Sodium borohydride → 1-Benzyl-4-(phenylamino)piperidine-4-methanol

HRID 37372노트

반응식

HRID 37372 반응식
[BH4-].[Na+].[C:3]1([NH:9][C:10]2([CH:23]=[O:24])[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CO.O>[C:3]1([NH:9][C:10]2([CH2:23][OH:24])[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

참가 물질

5

반응물 2

HCID 4311764Sodium borohydrideHCID 19935652HCID 19935652, 화합물

생성물 1

HCID 30172301-Benzyl-4-(phenylamino)piperidine-4-methanol수율 76%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

Sodium borohydride (2 g) was added portionwise to a stirred solution of 4-(N-phenylamino)-1-phenylmethyl-piperidine-4-carboxaldehyde (2 g) in methanol at room temperature. After stirring at room temperature for 2 hours the mixture was diluted with water, extracted with chloroform and the combined extracts washed and dried. After removal of the solvent, the crude product was purified by chromatography on silica gel, using chloroform/methanol (38:1) as eluant, to give the title compound (1.53 g) 4-(N-phenylamino)--1-phenylmethyl-4-piperidinylmethanol is then converted to sufentanil following the method described in U.S. Pat. No. 4,179,469 and as illustrated by FIG. 2.

후처리

  1. extractionextracted with chloroform
  2. washthe combined extracts washed
  3. customdried
  4. customAfter removal of the solvent
  5. customthe crude product was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-3f041f1a149f4c3da5afef44e7d0f088
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420280

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