5-Phenyl-3-[1-(phenylmethyl)-1,2,3,6-tetrahydro-4-pyridinyl]-1H-indole-7-carboxamide → 5-Phenyl-3-(4-piperidinyl)-1H-indole-7-carboxamide

HRID 2267484Notes

Reaction equation

HRID 2267484 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]3[C:13](=[C:14]([C:16]([NH2:18])=[O:17])[CH:15]=2)[NH:12][CH:11]=[C:10]3[C:19]2[CH2:20][CH2:21][N:22](CC3C=CC=CC=3)[CH2:23][CH:24]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>C(O)C.C(O)(=O)C.[OH-].[OH-].[Pd+2]>[C:1]1([C:7]2[CH:8]=[C:9]3[C:13](=[C:14]([C:16]([NH2:18])=[O:17])[CH:15]=2)[NH:12][CH:11]=[C:10]3[CH:19]2[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 114525415-Phenyl-3-[1-(phenylmethyl)-1,2,3,6-tetrahydro-4-pyridinyl]-1H-indole-7-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 114271625-Phenyl-3-(4-piperidinyl)-1H-indole-7-carboxamideYield 70%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

To the solution of 5-Phenyl-3-[1-(phenylmethyl)-1,2,3,6-tetrahydro-4-pyridinyl]-1H-indole-7-carboxamide (2.66 g, 6.5 mmol) in ethanol (150 mL) and acetic acid (3 mL) was added Pd(OH)2 (20% by weight on carbon) (0.8 g,) at ambient temperature. The solution was stirred under 1 atm of hydrogen for 2 days. The reaction mixture was then filtered through Celite, neutralized with 5% sodium hydroxide solution, and extracted with ethyl acetate. The solvent was removed under reduced pressure to yield the desired product (1.45 g, 70%).

Workup

  1. filtrationThe reaction mixture was then filtered through Celite
  2. extractionextracted with ethyl acetate
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-42ef280131644c6595fe4d34603f1261
Source dataset
uspto-grants-2010_12
Patent number
US07858796B2

Reaction notes

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