Hydrochloric Acid → HCID 19030903, compound

HRID 266822Notes

Reaction equation

HRID 266822 reaction equation
C([O:4][C:5]1[CH:29]=[CH:28][C:8]([C:9]([N:11]2[CH2:16][CH2:15][CH:14]([N:17]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:21][CH2:20][C:18]3=[O:19])[CH2:13][CH2:12]2)=[O:10])=[CH:7][CH:6]=1)C=C.Cl.CN(C)[C:33]1[CH:38]=CC=C[CH:34]=1>>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([C:9]([N:11]2[CH2:12][CH2:13][CH:14]([N:17]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:21][CH2:20][C:18]3=[O:19])[CH2:15][CH2:16]2)=[O:10])=[CH:28][C:29]=1[CH2:38][CH:33]=[CH2:34]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 949N,N-DimethylanilineHCID 19031254HCID 19031254, compound

Product 1

HCID 19030903HCID 19030903, compound

Procedure

1-[1-(4-Allyloxybenzoyl)-4-piperidinyl]-3,4-dihydrocarbostyril (1.15 g) is dissolved in N,N-dimethylaniline (5 ml) and the mixture is heated at 180°-190° C. for 8 hours. After cooling, the reaction mixture is adjusted to around pH 4 by adding hydrochloric acid thereto. The mixture is extracted with dichloromethane and dried with magnesium sulfate. The solvent is distilled off and the residue is purified by silica gel column chromatography (solvent: n-hexane:ethyl acetate=3:1→1:3) and further purified by silica gel column chromatography (solvent: dichloromethane:methanol=100:1) and recrystallized from dichloromethane/n-hexane to give 1-[1-(4-hydroxy-3-allylbenzoyl)-4-piperidinyl]-3,4-dihydrocarbostyril (0.22 g) as white powder, m.p.: 87°-90° C.

Workup

  1. temperaturethe mixture is heated at 180°-190° C. for 8 hours
  2. temperatureAfter cooling
  3. extractionThe mixture is extracted with dichloromethane
  4. dry with materialdried with magnesium sulfate
  5. distillationThe solvent is distilled off
  6. customthe residue is purified by silica gel column chromatography (solvent: n-hexane:ethyl acetate=3:1→1:3)
  7. customfurther purified by silica gel column chromatography (solvent: dichloromethane:methanol=100:1)
  8. customrecrystallized from dichloromethane/n-hexane

Sources & evidence

ORD record
ord-f9553653a67c45a192739a80f13ba119
Source dataset
uspto-grants-1997_07
Patent number
US05652247

Reaction notes

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