p-Toluenesulfonic acid monohydrate → HCID 54008509, compound

HRID 652971Notes

Reaction equation

HRID 652971 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][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]=[CH:7][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:16]=[CH:17][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:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[CH2:24][CH2:23]2)=[O:21])[CH:6]=[CH:7][C:8]=1[OH:9]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 53857309HCID 53857309, compound

Product 1

HCID 54008509HCID 54008509, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 650 mg (2.1 mmol) of N-(3-benzhydroxypropyl)piperazine in dry tetrahydrofuran (5 ml) was added a solution of 818 mg (2.1 mmol) of N-[5-[3methoxy-4-(β-methoxyethoxymethoxy)phenyl]-2,4-pentadienoyl]thiazolidihe-2-thione in dry tetrahydrofuran (6 ml) and the mixture was reacteed at room temperature for 14 hours. The reaction mixture was concentrated by evaporation under reduced pressure and the residue was diluted with chloroform. The mixture was washed, in turn, with 2N aqueous solution of sodium hydroxide and water and the organic layer was dried over anhydrous sodium sulfate and then concentrated by evaporation under reduced pressure. The residue was subjected to silica gel column chromatography, eluted with 1% methanol in chloroform, to give 1.106 g (1.8 mmol) of N-[5-[3-methoxy-4-(β-methoxyethoxymethoxy)phenyl]-2,4-pentadienoyl]-N'-(3-benzhydroxypropyl)piperazine. To a solution of 1.064 (2.1 mmol) of the amide compound in methanol (10 ml) was added 370 mg (1.95 mmol) of p-toluenesulfonic acid monohydrate, and the mixture was refluxed for 1.5 hous under argon atmosphere. The mixture was concentrated by evaporation under reduced pressure, diluted with chloroform and washed, in turn, with a saturated aqueous solution of sodium hydrogencarbonate and water. The organic layer was dried over anhydrous sodium sulfate and concentrated by evaporation under reduced pressure. The residue was subjected to silica gel column chromatography, eluted with a 1 to 2% methanol in chloroform, to give 730 mg (1.42 mmol) of N-[5-(3-methoxy-4-hydroxyphenyl)-2,4-pentadienoyl]-N'-(3-benzhydroxypropyl)piperazine.

Workup

  1. temperaturethe mixture was refluxed for 1.5 hous under argon atmosphere
  2. concentrationThe mixture was concentrated by evaporation under reduced pressure
  3. additiondiluted with chloroform
  4. washwashed, in turn, with a saturated aqueous solution of sodium hydrogencarbonate and water
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure
  7. washeluted with a 1 to 2% methanol in chloroform

Sources & evidence

ORD record
ord-1d0caf2cf8f3487badaea0b404102f94
Source dataset
uspto-grants-1987_06
Patent number
US04673684

Reaction notes

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