Ammonium formate → HCID 19030791, compound

HRID 266806Notes

Reaction equation

HRID 266806 reaction equation
[CH2:1]([N:8]([CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:38]=[CH:37][C:17]([C:18]([N:20]2[CH2:25][CH2:24][CH:23]([N:26]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH2:30][CH2:29][C:27]3=[O:28])[CH2:22][CH2:21]2)=[O:19])=[CH:16][CH:15]=1)C)C1C=CC=CC=1.C([O-])=O.[NH4+]>[C].[Pd].C(O)C>[CH3:1][NH:8][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:38]=[CH:37][C:17]([C:18]([N:20]2[CH2:25][CH2:24][CH:23]([N:26]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH2:30][CH2:29][C:27]3=[O:28])[CH2:22][CH2:21]2)=[O:19])=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 19031100HCID 19031100, compound

Product 1

HCID 19030791HCID 19030791, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-[1-{4-[3-(N-benzyl-N-methylamino)propoxy]benzoyl}-4-piperidinyl]-3,4-dihydrocarbostyril (5.3 g), 5% palladium-carbon (0.8 g), ammonium formate (2.6 g) and ethanol (300 ml) is refluxed with heating for 2 hours. The catalyst is filtered off and ethanol is distilled off under reduced pressure. To the residue is added chloroform and the mixture is washed successively with saturated sodium hydrogen carbonate, water and saline solution. Further the mixture is dried with sodium sulfate and the solvent is distilled off. The resulting residue is purified by silica gel column chromatography (solvent: dichloromethane:methanol=20:1→5:1) to give 1-[1-{4-[3-(N-methylamino)propoxy]benzoyl}-4-piperidinyl]-3,4-dihydrocarbostyril (4.37 g).

Workup

  1. temperatureis refluxed
  2. temperaturewith heating for 2 hours
  3. filtrationThe catalyst is filtered off
  4. distillationethanol is distilled off under reduced pressure
  5. additionTo the residue is added chloroform
  6. washthe mixture is washed successively with saturated sodium hydrogen carbonate, water and saline solution
  7. dry with materialFurther the mixture is dried with sodium sulfate
  8. distillationthe solvent is distilled off
  9. customThe resulting residue is purified by silica gel column chromatography (solvent: dichloromethane:methanol=20:1→5:1)

Sources & evidence

ORD record
ord-d40c3071901948908015bf337ce85055
Source dataset
uspto-grants-1997_07
Patent number
US05652247

Reaction notes

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