Trifluoroacetic acid → 4-(1-(4-fluorobenzyl)-1H-benzimidazole-2-carbonyl)piperidine

HRID 1647047Notes

Reaction equation

HRID 1647047 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[N:18]=[C:17]2[C:25]([CH:27]2[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]2)=[O:26])=[CH:11][CH:10]=1>CCOCC>[F:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[N:18]=[C:17]2[C:25]([CH:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[O:26])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 183333391-(t-butoxycarbonyl)-4-(1-(4-fluoro-benzyl)-1H-benzoimidazole-2-carbonyl)-piperidine

Product 1

HCID 155428834-(1-(4-fluorobenzyl)-1H-benzimidazole-2-carbonyl)piperidine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

With stirring, trifluoroacetic acid (10 ml) was added to 4-[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2- yl]carbonyl-1-piperidinecarboxylic acid, 1,1-dimethylethyl ester (1.65 g, 3.77×10-3 mole). After 30 minutes the reaction was cooled in an ice bath and ether (150 ml) was added. The flask was stoppered and placed in the refrigerator. After several hours, the solid was collected by filtration, washed with Et2O, and dried by suction. Crystallization from ethanol/ether afforded [1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]-4-piperidinylmethanone, mono (trifluoroacetate) as colorless needles: 1.45 g (84%), m.p. 213-215° C. (decomp).

Workup

  1. temperatureAfter 30 minutes the reaction was cooled in an ice bath
  2. waitAfter several hours
  3. filtrationthe solid was collected by filtration
  4. washwashed with Et2O
  5. customdried by suction
  6. customCrystallization from ethanol/ether

Sources & evidence

ORD record
ord-dbf84b387c8c4f8e9ea9c14b4c4ea040
Source dataset
uspto-grants-1993_01
Patent number
US05182399

Reaction notes

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