Sodium Hydroxide → HCID 19031140, compound

HRID 483485Notes

Reaction equation

HRID 483485 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-5bcee69c2b544396a8bfb22a539b5170
Source dataset
uspto-grants-1993_07
Patent number
US05225402

Reaction notes

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