Chloroacetyl chloride → N-((1-(2-chloroacetyl)piperidin-4-yl)methyl)-3,5-bis(trifluoromethyl)benzamide

HRID 388783Notes

Reaction equation

HRID 388783 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9](=[O:24])[C:10]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=2)[CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.[Cl:34][CH2:35][C:36](Cl)=[O:37]>C(Cl)Cl>[Cl:34][CH2:35][C:36]([N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9](=[O:24])[C:10]2[CH:11]=[C:12]([C:20]([F:21])([F:22])[F:23])[CH:13]=[C:14]([C:16]([F:18])([F:19])[F:17])[CH:15]=2)[CH2:3][CH2:2]1)=[O:37]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 81531DiisopropylethylamineHCID 57993323N-(piperidin-4-ylmethyl)-3,5-bis(trifluoromethyl)benzamide

Product 1

HCID 57993392N-((1-(2-chloroacetyl)piperidin-4-yl)methyl)-3,5-bis(trifluoromethyl)benzamideYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-(piperidin-4-ylmethyl)-3,5-bis(trifluoromethyl)benzamide (2.0 g, 5.66 mmol) and DIPEA (1.2 mL) in CH2Cl2 (10 mL) was added 2-chloroacetyl chloride (0.64, 5.66 mmol) dropwise, the mixture was stirred overnight. The mixture was washed with water, dried with Na2SO4, filtered, and the solvent was removed in vacuo. The residue was purified by automated flash chromatography to yield the product (2.0 g, 82%).

Workup

  1. washThe mixture was washed with water
  2. dry with materialdried with Na2SO4
  3. filtrationfiltered
  4. customthe solvent was removed in vacuo
  5. customThe residue was purified by automated flash chromatography

Sources & evidence

ORD record
ord-a2cce93bdd884a85acfb23711fb7d6a0
Source dataset
uspto-grants-2013_02
Patent number
US08377968B2

Reaction notes

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