Sodium Chloride → HCID 86741624, compound

HRID 652974Notes

Reaction equation

HRID 652974 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=[CH:21][C:22]([N:24]2[CH2:29][CH2:28][N:27]([CH2:30][CH2:31][O:32][CH:33]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:26][CH2:25]2)=[O:23])[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.[Cl-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=[CH:21][C:22]([N:24]2[CH2:25][CH2:26][N:27]([CH2:30][CH2:31][O:32][CH:33]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH2:28][CH2:29]2)=[O:23])[CH:6]=[C:7]([O:16][CH3:17])[C:8]=1[OH:9]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 10340Sodium CarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 54283397HCID 54283397, compound

Product 1

HCID 86741624HCID 86741624, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 413 mg (0.670 mmol) of of the amide compound in methanol (10 ml) was added 148 mg (0.778 mmol) of p-toluenesulfonic acid monohydrate, and the mixture was refluxed for 1 hour. A saturated aqueous solution of sodium chloride was added to the reaction mixture, which was adjusted to a pH value of 10 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 Sephadex column chromatography, eluted with methanol, to give 194 mg (0.367 mmol) of N-[5-(3,5-dimethoxy-4-hydroxyphenyl)-2,4-pentadienoyl)-N'-(2-benzhydroxyethyl)piperazine. Spectrophotometric data of the product support the structure shown below. ##STR111##

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. concentrationconcentrated by evaporation under reduced pressure
  5. washeluted with methanol

Sources & evidence

ORD record
ord-27e2fc481c9b42f3beee1215e51cb4e0
Source dataset
uspto-grants-1987_06
Patent number
US04673684

Reaction notes

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