Hydrochloric Acid → HCID 19030903, compound

HRID 1648584Notes

Reaction equation

HRID 1648584 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-f5bedd01a83f4c3cbd3ed60145701dca
Source dataset
uspto-grants-1995_07
Patent number
US05436254

Reaction notes

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