Water → HCID 178505674, compound

HRID 1756124Notes

Reaction equation

HRID 1756124 reaction equation
O.C([O-])=O.[NH4+].C([N:13]1[C:17]([CH2:18][CH2:19][CH2:20][CH:21]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:16][N:15]=[CH:14]1)C1C=CC=CC=1>C(O)C.[Pd]>[F:34][C:31]1[CH:32]=[CH:33][C:28]([CH:21]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:20][CH2:19][CH2:18][C:17]2[N:13]=[CH:14][NH:15][CH:16]=2)=[CH:29][CH:30]=1

Participants

6

Reactant 3

HCID 962WaterHCID 2723923Ammonium formateHCID 14822323HCID 14822323, compound

Product 1

HCID 178505674HCID 178505674, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A concentrated water solution of ammoniumformate (0,98 g, 15,6 mmol) is added dropwise to the boiling mixture of 1-benzyl-5-[4-(4-fluorophenyl)-4-phenylbutyl]-1H-imidazole (1,5 g, 3,9 mmol) and 10% Pd/C (0,156 g) in 16 ml of 50% ethanol. The mixture is refluxed for 2 hours. The catalyst is filtrated off and the solvent is evaporated. 2M NaOH is added and the product is extracted into ethyl acetate. The ethyl acetate phase is dried and evaporated to dryness to give the product. Yield 1,02 g. Melting point of the hydrochloride salt (from ethyl acetate) is 175°-182° C.

Workup

  1. temperatureThe mixture is refluxed for 2 hours
  2. filtrationThe catalyst is filtrated off
  3. customthe solvent is evaporated
  4. addition2M NaOH is added
  5. extractionthe product is extracted into ethyl acetate
  6. dry with materialThe ethyl acetate phase is dried
  7. customevaporated to dryness
  8. customto give the product
  9. customis 175°-182° C.

Sources & evidence

ORD record
ord-933ec43714ad4a41bbf51c38431c4ebc
Source dataset
uspto-grants-1995_08
Patent number
US05439928

Reaction notes

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