Thiophene → (+/-)-Methyl 1-(4-aminophenyl)-alpha-phenyl-4-piperidineacetate

HRID 1989863Notes

Reaction equation

HRID 1989863 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([CH:16]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:17]([O:19][CH3:20])=[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[CH2:15][CH2:14][CH:13]([CH:16]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:17]([O:19][CH3:20])=[O:18])[CH2:12][CH2:11]2)=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 8030ThiopheneHCID 22499408(+/-)-Methyl 1-(4-nitrophenyl)-alpha-phenyl-4-piperidineacetateHCID 178418361HCID 178418361, compound

Product 1

HCID 22499374(+/-)-Methyl 1-(4-aminophenyl)-alpha-phenyl-4-piperidineacetateYield 98.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of intermediate (17) (0.0022 mol) in methanol (100 ml) was hydrogenated at 50° C. with palladium on carbon (10%; 0.1 g) as a catalyst in the presence of a thiophene solution (4%; 0.1 ml). After uptake of hydrogen (3 equivalents), the catalyst was filtered off and the filtrate was evaporated. The residue was triturated in hexane. The precipitate was filtered off and dried, yielding 0.7 g (±)-methyl 1-(4-aminophenyl)-α-phenyl-4-piperidineacetate (intermediate 18, mp. 125° C.).

Workup

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

Sources & evidence

ORD record
ord-23e4564152724c2e876b710263bb8de9
Source dataset
uspto-grants-2010_01
Patent number
US07642378B2

Reaction notes

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