Thiophene → HCID 22499409, compound

HRID 1815526Notes

Reaction equation

HRID 1815526 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([CH:16]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:17]([NH:19][CH2:20][C:21]([F:24])([F:23])[F:22])=[O:18])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.S1C=CC=C1.[H][H]>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:11][CH2:12][N:13]([CH:16]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:17]([NH:19][CH2:20][C:21]([F:24])([F:23])[F:22])=[O:18])[CH2:14][CH2:15]2)=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 8030ThiopheneHCID 22499411HCID 22499411, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22499409HCID 22499409, compoundYield 70.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of intermediate (3) (0.0054 mole) in methanol (150 ml) was hydrogenated with Pd/C 10% (1 g) as a catalyst in the presence of a 4% thiophene solution (1 ml). After uptake of hydrogen (2 equivalents), the catalyst was filtered off and the filtrate was evaporated. The residue was triturated in DIPE. The precipitate was filtered off and dried, yielding 1.5 g of (±)-4-(4-aminophenyl)-α-phenyl-N-(2,2,2-trifluoroethyl)-1-piperazineacetamide (intermediate 4, melting point 136° C.).

Workup

  1. customthe filtrate was evaporated
  2. customThe residue was triturated in DIPE
  3. filtrationThe precipitate was filtered off
  4. customdried

Sources & evidence

ORD record
ord-4cb7502f5a384b07a7b5512da795dc34
Source dataset
uspto-grants-2005_04
Patent number
US06878724B2

Reaction notes

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