Water → HCID 127950, compound

HRID 652981Notes

Reaction equation

HRID 652981 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][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]=[CH:7][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:16]=[CH:17][CH:18]=[CH:19][C:20]([NH:22][CH2:23][CH2:24][N:25]2[CH2:26][CH2:27][CH:28]([O:31][CH:32]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH2:29][CH2:30]2)=[O:21])[CH:6]=[CH:7][C:8]=1[OH:9]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 54011209HCID 54011209, compound

Product 1

HCID 127950HCID 127950, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 690 mg (1.15 mmol) of the amide compound in methanol (14 ml) was added 212 mg (1.12 mmol) of p-toluenesulfonic acid monohydrate, and the mixture was refluxed for 25 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 (50:1), to give 393 mg (0.730 mmol) of 1-[2-[5-(3-methoxy-4-hydroxyphenyl)-2,4-pentadienoyl]aminoethyl]4-benzhydroxypiperidine.

Workup

  1. temperaturethe mixture was refluxed for 25 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 (50:1)

Sources & evidence

ORD record
ord-4598c67792524627b7b440fd0753955f
Source dataset
uspto-grants-1987_06
Patent number
US04673684

Reaction notes

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