Water → HCID 54172614, compound

HRID 652980Notes

Reaction equation

HRID 652980 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]([NH:22][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][CH:28]([O:31][CH:32]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:27][CH2:26]2)=[O:21])[CH:6]=[C:7]([O:16][CH3:17])[C:8]=1[O:9]COCCOC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O.C(=O)([O-])[O-].[Na+].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]([NH:22][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][CH:28]([O:31][CH:32]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH2:27][CH2:26]2)=[O:21])[CH:6]=[C:7]([O:16][CH3:17])[C:8]=1[OH:9]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 53819633HCID 53819633, compound

Product 1

HCID 54172614HCID 54172614, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 276 mg (0.456 mmol) of the amide compound in methanol (6 ml) was added 79 mg (0.415 mmol) of p-toluenesulfonic acid monohydrate, and the mixture was refluxed for 20 minutes. Water was added to the reaction mixture, which was adjusted to a pH value of 11 by the addition of an aqueous solution of sodium carbonate and then extracted with ethyl acetate. The organic layer was washed with water and concentrated by evaporation under reduced pressure. The residue was subjected to silica gel column chromatography, eluted with chloroform-methanol (20:1), to give 162 mg (0.299 mmol) of 1-[2-[3-(3,5-dimethoxy-4-hydroxyphenyl)-2-propenoyl]aminoethyl]-4-benzhydroxypiperidine.

Workup

  1. temperaturethe mixture was refluxed for 20 minutes
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. concentrationconcentrated by evaporation under reduced pressure
  5. washeluted with chloroform-methanol (20:1)

Sources & evidence

ORD record
ord-f51d418509fd4bd79c720775c3f03bd2
Source dataset
uspto-grants-1987_06
Patent number
US04673684

Reaction notes

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