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

HRID 37372ノート

反応式

HRID 37372 の反応式
[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

参加物

5

反応物 2

HCID 4311764Sodium borohydrideHCID 19935652HCID 19935652、化合物

生成物 1

HCID 30172301-Benzyl-4-(phenylamino)piperidine-4-methanol収率 76%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3f041f1a149f4c3da5afef44e7d0f088
出典データセット
uspto-grants-1995_05
特許番号
US05420280

反応ノート

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