Acrylic Acid → HCID 19030764, compound

HRID 1648598Notes

Reaction equation

HRID 1648598 reaction equation
[C:1]([OH:5])(=O)[CH:2]=[CH2:3].[CH2:6]([N:13]1[CH2:18][CH2:17][CH:16]([NH:19][C:20]2[CH2:25][CH2:24][CH2:23][C:22](=[O:26])[CH:21]=2)[CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(Cl)(Cl)Cl>[CH2:6]([N:13]1[CH2:18][CH2:17][CH:16]([N:19]2[C:20]3[CH2:21][CH2:3][CH2:2][C:1](=[O:5])[C:25]=3[CH2:24][CH2:23][C:22]2=[O:26])[CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 6581Acrylic AcidHCID 19030881HCID 19030881, compound

Product 1

HCID 19030764HCID 19030764, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Acrylic acid (28.9 ml) is added to 1-(1-benzyl-4-piperidinylamino)-1-cyclohexen-3-on (100 g) and the mixture is refluxed with stirring for 6 hours. After cooling, the reaction mixture is dissolved in chloroform containing 10 % methanol and purified by silica gel column chromatography (solvent; dichloromethane:methanol=40:1). The resultant is recrystallized from ethanol/water to give 1-(1-benzyl-4-piperidinyl)-5-oxo-3,4,5,6,7,8-hexahydrocarbostyril (23.98 g) as colorless needles, m.p.: 102°-103° C.

Workup

  1. temperaturethe mixture is refluxed
  2. temperatureAfter cooling
  3. custompurified by silica gel column chromatography (solvent; dichloromethane:methanol=40:1)
  4. customThe resultant is recrystallized from ethanol/water

Sources & evidence

ORD record
ord-d77b46fb129743029937c32bc2c5ca04
Source dataset
uspto-grants-1995_07
Patent number
US05436254

Reaction notes

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