[2-(dibenzylamino)-5,6-dihydro-7H-cyclopenta[b]pyridin-7-ylidene]acetonitrile → [2-(dibenzylamino)-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl]acetonitrile

HRID 887769Notes

Reaction equation

HRID 887769 reaction equation
[CH2:1]([N:8]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:9]1[N:14]=[C:13]2[C:15](=[CH:18][C:19]#[N:20])[CH2:16][CH2:17][C:12]2=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[OH-].[Pd+2].[OH-].[C]>[CH2:21]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]1[N:14]=[C:13]2[CH:15]([CH2:18][C:19]#[N:20])[CH2:16][CH2:17][C:12]2=[CH:11][CH:10]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 1

HCID 68702395[2-(dibenzylamino)-5,6-dihydro-7H-cyclopenta[b]pyridin-7-ylidene]acetonitrile

Product 1

HCID 59145908[2-(dibenzylamino)-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl]acetonitrile

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 887MethanolSolvent

Procedure

[2-(Dibenzylamino)-5,6-dihydro-7H-cyclopenta[b]pyridin-7-ylidene]acetonitrile (1.01 g, 2.87 mmol) was dissolved in methanol (40 mL), 20% palladium hydroxide-carbon powder (200 mg) was added, and the mixture was stirred under a hydrogen atmosphere at room temperature for 60 hr. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound. The obtained title compound was used for the reaction of Reference Example 34 without purification.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-75598dfec06a48108b7c29757e181518
Source dataset
uspto-grants-2012_08
Patent number
US08247429B2

Reaction notes

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