Sodium Hydroxide → HCID 19031140, compound

HRID 1648541Notes

Reaction equation

HRID 1648541 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([NH:25]C(=O)C)[CH:23]=3)[CH:18]=[CH:17][C:15]2=[O:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([NH2:25])[CH:23]=3)[CH:18]=[CH:17][C:15]2=[O:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19030731HCID 19030731, compound

Product 1

HCID 19031140HCID 19031140, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 1-(1-benzyl-4-piperidinyl)-7-acetylaminocarbostyril (3.0 g) are added ethanol (32 ml) and an aqueous 10 % sodium hydroxide solution (32 ml) and the mixture is refluxed for 1 hour. After the reaction mixture is concentrated by distilling off the solvent, water is added to the residue and the resulting solution is extracted with dichloromethane. The extract is concentrated by distilling off the solvent and recrystallized from ethanol/chloroform to give 1-(1-benzyl-4-piperidinyl)-7-aminocarbostyril (2.4 g) as white powders, m.p. 238°-241° C.

Workup

  1. concentrationAfter the reaction mixture is concentrated
  2. distillationby distilling off the solvent, water
  3. additionis added to the residue
  4. extractionthe resulting solution is extracted with dichloromethane
  5. concentrationThe extract is concentrated
  6. distillationby distilling off the solvent
  7. customrecrystallized from ethanol/chloroform

Sources & evidence

ORD record
ord-7e492518c1d948c99e0e97e59e999483
Source dataset
uspto-grants-1995_07
Patent number
US05436254

Reaction notes

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