HCID 14010733, compound → HCID 14010737, compound

HRID 255661Notes

Reaction equation

HRID 255661 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[N:18]([C:28]3[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][C:29]=3[CH3:35])[CH:19]=[C:20]([C:25](=[O:27])[CH:26]=2)[C:21]([O:23][CH3:24])=[O:22])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>CO.[C].[Pd]>[NH:11]1[CH2:16][CH2:15][CH:14]([C:17]2[N:18]([C:28]3[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][C:29]=3[CH3:35])[CH:19]=[C:20]([C:25](=[O:27])[CH:26]=2)[C:21]([O:23][CH3:24])=[O:22])[CH2:13][CH2:12]1

Participants

4

Reactant 1

HCID 14010733HCID 14010733, compound

Product 1

HCID 14010737HCID 14010737, compoundYield 83.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent2×

Procedure

5 ml of methanol was carefully added to 0.06 g of 5% by weight palladium carbon under ice cooling, and this mixture was stirred under a hydrogen atomosphere at room temperature for 20 minutes, followed by addition of a solution of 0.4 g of methyl 6-(1-benzyloxycarbonyl-4-piperidinyl)-1-(4-hydroxy-2-methylphenyl)-4-oxo-1,4-dihydronicotinate in 2 ml of methanol, and the mixture was subjected to hydrogenation under atmospheric pressure for 4 hours. After completion of the reaction, the palladium carbon was removed by filtration and the solvent was removed by distillation under reduced pressure to obtain 0.24 g of methyl 6-(4-piperidinyl)-1-(4-hydroxy-2-methylphenyl)-4-oxo-1,4-dihydronicotinate having a melting point of 226°-228° C.

Workup

  1. waitthe mixture was subjected to hydrogenation under atmospheric pressure for 4 hours
  2. customAfter completion of the reaction
  3. customthe palladium carbon was removed by filtration
  4. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-b37af003e8114220872dce24f6b13e8e
Source dataset
uspto-grants-1987_10
Patent number
US04698352

Reaction notes

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