Ethanol → 4-amino-3-chloro-N-(1-methyl-4-piperidyl)benzamide

HRID 2234373Notes

Reaction equation

HRID 2234373 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[N+:18]([O-])=O)[C:5]([NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]1)=[O:6].CCO>[Pt].C(Cl)Cl>[NH2:18][C:17]1[CH:16]=[CH:15][C:4]([C:5]([NH:7][CH:8]2[CH2:9][CH2:10][N:11]([CH3:14])[CH2:12][CH2:13]2)=[O:6])=[CH:3][C:2]=1[Cl:1]

Participants

5

Reactant 2

HCID 702EthanolHCID 686867193-chloro-N-(1-methyl-4-piperidyl)-4-nitro-benzamide2×

Product 1

HCID 580150334-amino-3-chloro-N-(1-methyl-4-piperidyl)benzamideYield 100.8%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6344DichloromethaneSolvent

Procedure

3-chloro-N-(1-methyl-4-piperidyl)-4-nitro-benzamide (Intermediate 56; 1.8 g, 6 mmol) hydrogenated over 2 hours with agitation at 298K and pressure of 5 bar using a 5% Pt/C catalyst and EtOH (50 mL) solvent. The catalyst was filtered and the filtrate concentrated to give a yellow crystalline solid which was dissolved in DCM and purified by column chromatography (5% MeOH/DCM) to give the title compound as a pale yellow crystalline solid (1.62 g, 100%)

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate concentrated
  3. customto give a yellow crystalline solid which
  4. custompurified by column chromatography (5% MeOH/DCM)

Sources & evidence

ORD record
ord-9fa46753bc5b44a7bc1d74127dd28b92
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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