8-nitro-6-{4-[N-methyl-N-(2-phenylethyl)amino]-1-piperidinylcarbonyl}-3,4-dihydrocarbostyril → 8-amino-6-{4-[N-methyl-N-(2-phenylethyl)amino]-1-piperidinylcarbonyl}-3,4-dihydrocarbostyril

HRID 232717Notes

Reaction equation

HRID 232717 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:15]([N:17]2[CH2:22][CH2:21][CH:20]([N:23]([CH3:32])[CH2:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:19][CH2:18]2)=[O:16])[CH:7]=[C:8]2[C:13]=1[NH:12][C:11](=[O:14])[CH2:10][CH2:9]2)([O-])=O>C(O)C.[C].[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([C:15]([N:17]2[CH2:22][CH2:21][CH:20]([N:23]([CH3:32])[CH2:24][CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:19][CH2:18]2)=[O:16])[CH:7]=[C:8]2[C:13]=1[NH:12][C:11](=[O:14])[CH2:10][CH2:9]2

Participants

4

Reactant 1

HCID 110591838-nitro-6-{4-[N-methyl-N-(2-phenylethyl)amino]-1-piperidinylcarbonyl}-3,4-dihydrocarbostyril

Product 1

HCID 233590718-amino-6-{4-[N-methyl-N-(2-phenylethyl)amino]-1-piperidinylcarbonyl}-3,4-dihydrocarbostyrilYield 98.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

0.5 g of 5% palladium-carbon was suspended in 0 ml of ethanol. Thereto was added 5 g of 8-nitro-6-{4-[N-methyl-N-(2-phenylethyl)amino]-1-piperidinylcarbonyl}-3,4-dihydrocarbostyril. The mixture was subjected to catalytic reduction at 30°-40° C. at normal pressure in a water bath. After the completion of hydrogen absorption, the reaction mixture was filtered to remove the catalyst. The catalyst was washed with ethanol. The filtrate and the washings were mixed. The mixture was subjected to distillation to remove the solvent to obtain 4.6 g of 8-amino-6-{4-[N-methyl-N-(2-phenylethyl)amino]-1-piperidinylcarbonyl}-3,4-dihydrocarbostyril as a white amorphous.

Workup

  1. customThe mixture was subjected to catalytic reduction at 30°-40° C. at normal pressure in a water bath
  2. customAfter the completion of hydrogen absorption
  3. filtrationthe reaction mixture was filtered
  4. customto remove the catalyst
  5. washThe catalyst was washed with ethanol
  6. additionThe filtrate and the washings were mixed
  7. distillationThe mixture was subjected to distillation
  8. customto remove the solvent

Sources & evidence

ORD record
ord-84378bda3add43f7b376b7ec35f571b4
Source dataset
uspto-grants-1997_01
Patent number
US05591751

Reaction notes

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