(E)-N-(5,6-dihydro-7H-cyclopenta[d]pyrimidin-4-yl)-4-[4-(1-benzylpiperidin-4-yl)-2-butenoyl]aniline → N-(5,6-dihydro-7H-cyclopenta[d]pyrimidin-4-yl)-4-[4-(1-benzylpiperidin-4-yl)butanoyl]aniline

HRID 976134Notes

Reaction equation

HRID 976134 reaction equation
[N:1]1[C:6]2[CH2:7][CH2:8][CH2:9][C:5]=2[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17](=[O:34])/[CH:18]=[CH:19]/[CH2:20][CH:21]3[CH2:26][CH2:25][N:24]([CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH2:23][CH2:22]3)=[CH:13][CH:12]=2)=[N:3][CH:2]=1>[Pt]=O.C(O)C>[N:1]1[C:6]2[CH2:7][CH2:8][CH2:9][C:5]=2[C:4]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([C:17](=[O:34])[CH2:18][CH2:19][CH2:20][CH:21]3[CH2:26][CH2:25][N:24]([CH2:27][C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH2:23][CH2:22]3)=[CH:15][CH:16]=2)=[N:3][CH:2]=1

Participants

4

Reactant 1

HCID 19968897(E)-N-(5,6-dihydro-7H-cyclopenta[d]pyrimidin-4-yl)-4-[4-(1-benzylpiperidin-4-yl)-2-butenoyl]aniline

Product 1

HCID 19968926N-(5,6-dihydro-7H-cyclopenta[d]pyrimidin-4-yl)-4-[4-(1-benzylpiperidin-4-yl)butanoyl]anilineYield 78.8%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

30 ml of ethanol and 0.1 g of platinum oxide were added to 0.24 g of (E)-N-(5,6-dihydro-7H-cyclopenta[d]pyrimidin-4-yl)-4-[4-(1-benzylpiperidin-4-yl)-2-butenoyl]aniline, and the mixture was stirred at room temperature under a hydrogen stream for 45 minutes. After removing the solid by filtration, the solvent was removed by distillation and the obtained residue was applied to silica gel column chromatography to obtain 0.19 g of the title compound as white powder.

Workup

  1. customAfter removing the solid
  2. filtrationby filtration
  3. customthe solvent was removed by distillation

Sources & evidence

ORD record
ord-b1ae639c5410425bb5306b17bc92be40
Source dataset
uspto-grants-1997_03
Patent number
US05610303

Reaction notes

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