Ammonium formate → HCID 66649874, compound

HRID 419718Notes

Reaction equation

HRID 419718 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[NH:15][C:16]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([C:26]([F:29])([F:28])[F:27])[CH:20]=3)=[CH:17][N:18]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.[NH4+].C([O-])=O>[OH-].[OH-].[Pd+2].CO>[F:25][C:22]1[CH:23]=[CH:24][C:19]([C:16]2[NH:15][C:14]([N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[N:18][CH:17]=2)=[CH:20][C:21]=1[C:26]([F:29])([F:27])[F:28]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 66649865HCID 66649865, compound

Product 1

HCID 66649874HCID 66649874, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Combine 1-Benzyl-4-[5-(4-fluoro-3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-piperazine (260 mg, 1.00 equiv; 0.643 mmoles), 20 wt % Pd(OH)2/C Degussa E101NE/W (250 mg); methanol (10 mL), formic acid, ammonium salt (20 equiv, 12.8 mmoles; 810 mg) and heated to 50° C. for 2 hours, then cooled to room temperature. Filter the reaction mixture through Celite®, evaporate under reduced pressure and coevaporate once with methanol to give 195.2 mg (0.621 mmol, 97%) 1-[5-(4-Fluoro-3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-piperazine as a yellow foam.

Workup

  1. filtrationFilter the reaction mixture through Celite®
  2. customevaporate under reduced pressure and coevaporate once with methanol

Sources & evidence

ORD record
ord-493017390f504d0bac9761d6df91c5e9
Source dataset
uspto-grants-2012_01
Patent number
US08093383B2

Reaction notes

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