Benzoyl chloride, 3-chloro- → HCID 68304436, compound

HRID 1846673Notes

Reaction equation

HRID 1846673 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH2:18])[CH2:8][CH2:7]1)[CH3:2].[Cl:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[C:24](Cl)=[O:25]>C(#N)C>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][CH:6]1[CH2:7][CH2:8][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH:18][C:24](=[O:25])[C:23]2[CH:27]=[CH:28][CH:29]=[C:21]([Cl:20])[CH:22]=2)[CH2:10][CH2:11]1)[CH3:2]

Participants

4

Reactant 2

HCID 69252Benzoyl chloride, 3-chloro-HCID 57960164HCID 57960164, compound

Product 1

HCID 68304436HCID 68304436, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 0.500 g (1.91 mmol) of [1-(2-amino-phenyl)-piperidin-4-yl]-acetic acid ethyl ester in acetonitrile (100 mL) is added 0.25 mL (1.9 mmol) of 3-chlorobenzoyl chloride. The mixture is stirred at room temperature overnight. The mixture is concentrated under reduced pressure and the residue is purified by flash silica gel chromatography to provide 0.34 g (44%) of {1-[2-(3-chloro-benzoylamino)-phenyl]-piperidin-4-yl}-acetic acid ethyl ester as a clear oil.

Workup

  1. concentrationThe mixture is concentrated under reduced pressure
  2. customthe residue is purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-6ce83dd5bb384272b92aea62f7ed9cfd
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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