Trifluoroacetic acid → N-(3,3-difluorocyclobutyl)-3-(piperazin-1-ylmethyl)benzamide

HRID 1878434Notes

Reaction equation

HRID 1878434 reaction equation
[F:1][C:2]1([F:29])[CH2:5][CH:4]([NH:6][C:7]([C:9]2[CH:10]=[C:11]([CH:26]=[CH:27][CH:28]=2)[CH2:12][N:13]2[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]2)=[O:8])[CH2:3]1.FC(F)(F)C(O)=O>ClCCl>[F:29][C:2]1([F:1])[CH2:5][CH:4]([NH:6][C:7](=[O:8])[C:9]2[CH:28]=[CH:27][CH:26]=[C:11]([CH2:12][N:13]3[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]3)[CH:10]=2)[CH2:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57917660HCID 57917660, compound

Product 1

HCID 57917681N-(3,3-difluorocyclobutyl)-3-(piperazin-1-ylmethyl)benzamideYield 81.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(3-(3,3-difluorocyclobutylcarbamoyl)benzyl)piperazine-1-carboxylate (12.65 mmol, 5.179 g) was stirred at room temperature in dichloromethane (10 mL)/trifluoroacetic acid (10 mL) for 1 hour with sonication. The solvent was removed under vacuum and the resulting residue was purified by strong cation exchange column chromatography to afford the title compound (3.19 g). MS (ESI) m/z 310.4 [M+H]+

Workup

  1. customwith sonication
  2. customThe solvent was removed under vacuum
  3. customthe resulting residue was purified by strong cation exchange column chromatography

Sources & evidence

ORD record
ord-1becd9dc5c424d3aa0def01a9a8a43f0
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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