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

HRID 508641Notes

Reaction equation

HRID 508641 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-a6253b82129c424d878c67049b19f0a5
Source dataset
uspto-grants-2015_08
Patent number
US09096522B2

Reaction notes

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