Sulfuric Acid → 1-(1-Benzyl-4-piperidinyl)carbostyril

HRID 483484Notes

Reaction equation

HRID 483484 reaction equation
S(=O)(=O)(O)O.C(O[CH:9]=[CH:10][C:11]([N:13]([CH:20]1[CH2:25][CH2:24][N:23]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:22][CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:12])C.[OH-].[Na+]>>[CH2:26]([N:23]1[CH2:24][CH2:25][CH:20]([N:13]2[C:14]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:9]=[CH:10][C:11]2=[O:12])[CH2:21][CH2:22]1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 54194521N-(beta-ethoxyacryloyl)-N-(1-benzyl-4-piperidinyl)aniline

Product 1

HCID 149695661-(1-Benzyl-4-piperidinyl)carbostyrilYield 83.2%

Procedure

To a concentrated sulfuric acid (15 ml) is added in portions N-(β-ethoxyacryloyl)-N-(1-benzyl-4-piperidinyl)aniline (1.1 g) at 60° C. After stirring the mixture at the same temperature for 15 minutes, the reaction mixture is poured into ice-water, made alkaline with a 10% aqueous sodium hydroxide solution and extracted with dichloromethane. After the extract is concentrated by distilling off the solvent, the resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=50:1) and recrystallized from ethyl acetate to give 1-(1-benzyl-4-piperidinyl)carbostyril (0.8 g) as white powders, m.p. 97°-99° C.

Workup

  1. extractionextracted with dichloromethane
  2. concentrationAfter the extract is concentrated
  3. distillationby distilling off the solvent
  4. customthe resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=50:1)
  5. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-afdc8ea177f3494893453c0a9e78fb07
Source dataset
uspto-grants-1993_07
Patent number
US05225402

Reaction notes

Loading…