Trifluoroacetic acid → 3-(piperazin-1-ylmethyl)-N-(1,1,1-trifluoro-2-methylpropan-2-yl)benzamide

HRID 1878418Notes

Reaction equation

HRID 1878418 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]([NH:6][C:7]([C:9]1[CH:10]=[C:11]([CH:26]=[CH:27][CH:28]=1)[CH2:12][N:13]1[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]1)=[O:8])([CH3:5])[CH3:4].FC(F)(F)C(O)=O>ClCCl>[N:13]1([CH2:12][C:11]2[CH:10]=[C:9]([CH:28]=[CH:27][CH:26]=2)[C:7]([NH:6][C:3]([CH3:5])([CH3:4])[C:2]([F:29])([F:1])[F:30])=[O:8])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86635136tert-Butyl 4-(3-(1,1,1-trifluoro-2-methylpropan-2-ylcarbamoyl)benzyl)piperazine-1-carboxylate

Product 1

HCID 668782073-(piperazin-1-ylmethyl)-N-(1,1,1-trifluoro-2-methylpropan-2-yl)benzamideYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

tert-Butyl 4-(3-(1,1,1-trifluoro-2-methylpropan-2-ylcarbamoyl)benzyl)piperazine-1-carboxylate (0.792 mmol, 340 mg) wsa dissolved in dichloromethane (3 mL) and trifluoroacetic acid (7.92 mmol, 0.588 ml, 903 mg) added. After 2 hours stirring, the mixture was taken up in dichloromethane, loaded on to a strong cation exchange column (5 g) and washed with dichloromethane/methanol. Elution of the column with 2M ammonia in methanol gave the title compound (260 mg). MS (ESI) m/z 330.3 [M+H]+

Workup

  1. washwashed with dichloromethane/methanol
  2. washElution of the column with 2M ammonia in methanol

Sources & evidence

ORD record
ord-a2fbf00256f14b7a9f4d4efb23392d8b
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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