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

HRID 1737066Notes

Reaction equation

HRID 1737066 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-714cf736ddaa4b2a8ab39d1fe76b1119
Source dataset
uspto-grants-1996_07
Patent number
US05541195

Reaction notes

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