Ammonia → HCID 19030729, compound

HRID 483512Notes

Reaction equation

HRID 483512 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[C:8]([CH:28]=[CH:29][CH:30]=1)[C:9]([N:11]1[CH2:16][CH2:15][CH:14]([N:17]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:21][CH2:20][C:18]2=[O:19])[CH2:13][CH2:12]1)=[O:10])=O)C.[NH3:31].[Cl-].[NH4+]>C(O)C>[C:4]([C:6]1[CH:7]=[C:8]([CH:28]=[CH:29][CH:30]=1)[C:9]([N:11]1[CH2:16][CH2:15][CH:14]([N:17]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:21][CH2:20][C:18]2=[O:19])[CH2:13][CH2:12]1)=[O:10])(=[O:3])[NH2:31]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 19031179HCID 19031179, compound

Product 1

HCID 19030729HCID 19030729, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-[1-(3-Ethoxycarbonylbenzoyl)-4-piperidinyl]-3,4-dihydrocarbostyril (0.5 g), aqueous ammonia (10 ml) and ammonium chloride (the effective amount as a catalyst) are dissolved in ethanol (10 ml) and the mixture is stirred at 110°-130° C. for 10 hours in an autoclave. Ethanol is distilled off under reduced pressure and the residue is extracted with methylene chloride. The organic layer is washed with water and saturated saline solution, dried with sodium sulfate and concentrated. The solvent is distilled off and the resulting residue is purified by silica gel column chromatography (solvent: methylene chloride:methanol=10:1) to give 1-[1-(3-carbamoylbenzoyl)-4-piperidinyl]-3,4-dihydrocarbostyril (0.15 g).

Workup

  1. distillationEthanol is distilled off under reduced pressure
  2. extractionthe residue is extracted with methylene chloride
  3. washThe organic layer is washed with water and saturated saline solution
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated
  6. distillationThe solvent is distilled off
  7. customthe resulting residue is purified by silica gel column chromatography (solvent: methylene chloride:methanol=10:1)

Sources & evidence

ORD record
ord-ec83d3d28af14a8eb44a0bd9d12bbcc1
Source dataset
uspto-grants-1993_07
Patent number
US05225402

Reaction notes

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