Sulfuric Acid → HCID 19031064, compound

HRID 266789Notes

Reaction equation

HRID 266789 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]([C:26](=[O:33])[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>>[C:26]([N:23]1[CH2:24][CH2:25][CH:20]([N:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:9]=[CH:10][C:11]2=[O:12])[CH2:21][CH2:22]1)(=[O:33])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 54255408HCID 54255408, compound

Product 1

HCID 19031064HCID 19031064, compoundYield 75.4%

Procedure

Conc. sulfuric acid (8 ml) is added to N-(β-ethoxyacryloyl)-N-(1-benzoyl-4-piperidinyl)aniline (0.8 g) and the mixture is reacted at 60° C. for 30 minutes. The reaction mixture is poured into ice-water and then extracted with dichloromethane. The solvent is concentrated and the resulting residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol=50:1) to give 1-(1-benzoyl-4-piperidinyl)carbostyril (0.53 g).

Workup

  1. customthe mixture is reacted at 60° C. for 30 minutes
  2. extractionextracted with dichloromethane
  3. concentrationThe solvent is concentrated
  4. customthe resulting residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol=50:1)

Sources & evidence

ORD record
ord-33a2d2f41a8443009fdb5bc0a22eee9d
Source dataset
uspto-grants-1997_07
Patent number
US05652247

Reaction notes

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