4-(3-Ethylbenzo[b]thiophen-2-yl)-1,2,5,6-tetrahydropyridine → 4-(3-Ethylbenzo[b]thiophen-2-yl)piperidine

HRID 1837483Notes

Reaction equation

HRID 1837483 reaction equation
[CH2:1]([C:3]1[C:4]2[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=2[S:6][C:7]=1[C:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH:9]=1)[CH3:2]>C(O)C.FC(F)(F)CO.[Pd]>[CH2:1]([C:3]1[C:4]2[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=2[S:6][C:7]=1[CH:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1)[CH3:2]

Participants

5

Reactant 1

HCID 129927714-(3-Ethylbenzo[b]thiophen-2-yl)-1,2,5,6-tetrahydropyridine

Product 1

HCID 129927724-(3-Ethylbenzo[b]thiophen-2-yl)piperidineYield 84.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 64092,2,2-TrifluoroethanolSolvent

Procedure

Scheme IA, Step C: To a mixture of 4-(3-ethylbenzo[b]thiophen-2-yl)-1,2,5,6-tetrahydropyridine (0.465 g, 1.91 mmol) in ethanol (15 mL) and 2,2,2-trifluoroethanol (5 mL) was added 10% palladium on carbon (0.25 g). The mixture was hydrogenated at one atmosphere for 24 hours. The mixture was carefully filtered and evaporated to give the intermediate title compound as a yellow amorphous solid (0.395 g, 84%). FDMS m/e=246 (M++1).

Workup

  1. filtrationThe mixture was carefully filtered
  2. customevaporated

Sources & evidence

ORD record
ord-b8daefeb693f428d8fbf05f0f3e0306d
Source dataset
uspto-grants-2004_08
Patent number
US06784180B2

Reaction notes

Loading…