Ammonia → (2R*,4S*)-2-(4-chlorobenzyl)-1-(3,5-dimethylbenzoyl)-4-piperidinamine

HRID 1033369노트

반응식

HRID 1033369 반응식
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][C@@H:7]2[CH2:12][C@@H:11]([NH:13]C(=O)C)[CH2:10][CH2:9][N:8]2[C:17](=[O:26])[C:18]2[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([CH3:25])[CH:19]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].ClCCl.CO.N>Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C@@H:7]2[CH2:12][C@@H:11]([NH2:13])[CH2:10][CH2:9][N:8]2[C:17](=[O:26])[C:18]2[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([CH3:25])[CH:19]=2)=[CH:27][CH:28]=1

참가 물질

6

반응물 4

HCID 222AmmoniaHCID 10340Sodium CarbonateHCID 21226129Dichloromethane methanolHCID 57050444(2R*,4S*)-2-(4-chlorobenzyl)-1-(3,5-dimethylbenzoyl)-N-acetyl-4-piperidinamine

생성물 1

HCID 57322251(2R*,4S*)-2-(4-chlorobenzyl)-1-(3,5-dimethylbenzoyl)-4-piperidinamine

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

실험 절차

A suspension of 730 mg (1.83 mmol) of (2R*,4S*)-2-(4-chlorobenzyl)-1-(3,5-dimethylbenzoyl)-N-acetyl-4-piperidinamine in 6N hydrochloric acid is heated at 100°for 16 hours, during which the starting material dissolves. The reaction mixture is basified with 10% strength aqueous sodium carbonate solution and extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate and evaporated to dryness under reduced pressure. The crude title compound is purified by chromatography on silica gel with dichloromethane/methanol/25% strength ammonia solution (90:10:0.1) as mobile phase and is obtained as almost colourless resin. TLC (dichloromethane/methanol/25% strength ammonia solution; 90:10:0.1): Rf =0.26;FD-MS: (M+1)+=357

후처리

  1. temperatureis heated at 100°for 16 hours, during which the starting material
  2. dissolutiondissolves
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. customevaporated to dryness under reduced pressure
  6. customThe crude title compound is purified by chromatography on silica gel with dichloromethane/methanol/25% strength ammonia solution (90:10:0.1) as mobile phase
  7. customis obtained as almost colourless resin

출처 및 근거

ORD 기록
ord-f770a041254d4944a61542c91e73fc5b
출처 데이터셋
uspto-grants-1994_05
특허 번호
US05310743

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