Water → HCID 53979608, compound

HRID 652979Notes

Reaction equation

HRID 652979 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][C:18]([NH:20][CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][CH:26]([O:29][CH:30]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:25][CH2:24]2)=[O:19])[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][C:18]([NH:20][CH2:21][CH2:22][N:23]2[CH2:24][CH2:25][CH:26]([O:29][CH:30]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:27][CH2:28]2)=[O:19])[CH:6]=[CH:7][C:8]=1[OH:9]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 54408392HCID 54408392, compound

Product 1

HCID 53979608HCID 53979608, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 292 mg (0.508 mmol) of the amide compound in methanol (8 ml) was added 112 mg (0.589 mmol) of p-toluenesulfonic acid monohydrate, and the mixture was refluxed for 20 minites. 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 164 mg (0.337 mmol) of 1-[2-[3-(3-methoxy-4-hydroxyphenyl)-2-propenoyl]aminoethyl]-4-benzhydroxypiperidine.

Workup

  1. temperaturethe mixture was refluxed for 20 minites
  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-5057a629bd894e71b994dba2081aab67
Source dataset
uspto-grants-1987_06
Patent number
US04673684

Reaction notes

Loading…