p-Toluenesulfonic acid monohydrate → N-[3-(3,5-dimethoxy-4-hydroxyphenyl) 2-propenoyl]-N'-(3-benzhydroxypropyl)piperazine

HRID 652968Notes

Reaction equation

HRID 652968 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]([N:22]2[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][CH2:30][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)[CH2:24][CH2:23]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>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]([N:22]2[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][CH2:30][O:31][CH:32]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:24][CH2:23]2)=[O:21])[CH:6]=[C:7]([O:16][CH3:17])[C:8]=1[OH:9]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 53774023N-[3-[3,5-dimethoxy-4-(beta-methoxyethoxymethoxy) phenyl]-2-propenoyl]-N'-(3-benzhydroxypropyl)piperazine

Product 1

HCID 54135289N-[3-(3,5-dimethoxy-4-hydroxyphenyl) 2-propenoyl]-N'-(3-benzhydroxypropyl)piperazineYield 84.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 270 mg (0.45 mmol) of the amide compound in 5 ml of methanol was added 95 mg (0.5 mmol) of p-toluen esulfonic acid monohydrate,,and the mixture was heated and refluxed for 1 hour under argon atmosphere. The reaction mixture was concentrated by evaporation under reduced pressure, a saturated aqueous solution of sodium hydrcgencarbonate was added to the residue, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated by evaporation under reduced pressure. The residue was subjected tc silica gel column chromatography, eluted with chlcroform - methanol, to give 200 mg (0.38 mmol) of N-[3-(3,5-dimethoxy-4-hydroxyphenyl) 2-propenoyl]-N'-(3-benzhydroxypropyl)piperazine. Spectrophotometric data of the product support the structure shown below. ##STR93##

Workup

  1. temperaturethe mixture was heated
  2. temperaturerefluxed for 1 hour under argon atmosphere
  3. concentrationThe reaction mixture was concentrated by evaporation under reduced pressure
  4. additiona saturated aqueous solution of sodium hydrcgencarbonate was added to the residue
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated by evaporation under reduced pressure
  8. washeluted with chlcroform - methanol

Sources & evidence

ORD record
ord-5928e1ed38bc4e4fbf1e52e79216ebf8
Source dataset
uspto-grants-1987_06
Patent number
US04673684

Reaction notes

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