Thiophene → HCID 53677180, compound

HRID 580896Notes

Reaction equation

HRID 580896 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14]1.S1C=CC=C1>[Pd].C(OC(C)C)(C)C.CO>[N:13]1([CH:2]2[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]2)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14]1

Participants

7

Reactant 3

HCID 8030ThiopheneHCID 10328IndolineHCID 34767Ethyl 4-oxo-1-piperidinecarboxylate

Product 1

HCID 53677180HCID 53677180, compoundYield 58.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 7914Diisopropyl EtherSolvent

Procedure

A mixture of ethyl 4-oxo-1-piperidinecarboxylate (85 g) and 2,3-dihydro-1H-indole (60 g), palladium on activated carbon (10%) (4 g) and a solution of thiophene in isopropyl ether (4%) (2 ml) in methanol (700 ml) was reacted in a Parr Pressure Vessel at 50° C. overnight. After completion, the mixture was filtered and the filtrate was evaporated, yielding 80 g (58%) of ethyl 4-(2,3-dihydro-1Hindol-1-yl)-1-piperidine-carboxylate (intermediate 6)

Workup

  1. filtrationAfter completion, the mixture was filtered
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-5e384a7bdba14878a304853ff56edd72
Source dataset
uspto-grants-1999_07
Patent number
US05919788

Reaction notes

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