Water → HCID 54090577, compound

HRID 652955Notes

Reaction equation

HRID 652955 reaction equation
[CH:1]([N:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][NH:22][C:23](=[O:48])[CH:24]=[CH:25][CH:26]=[CH:27][C:28]2[CH:33]=[CH:32][C:31]([O:34]COCCOC)=[C:30]([O:41]COCCOC)[CH:29]=2)[CH2:16][CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O.C(=O)([O-])[O-].[Na+].[Na+]>CO>[CH:1]([N:14]1[CH2:15][CH2:16][N:17]([CH2:20][CH2:21][NH:22][C:23](=[O:48])[CH:24]=[CH:25][CH:26]=[CH:27][C:28]2[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([OH:41])[CH:29]=2)[CH2:18][CH2:19]1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 54276165HCID 54276165, compound

Product 1

HCID 54090577HCID 54090577, compoundYield 47.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 289 mg (0.438 mmol) of the amide compound prepared above in methanol (10 ml) was added 127 mg (0.668 mmol) of p-toluenesulfonic acid hydrate. The mixture was refluxed in an argon atmosphere for 7 hours. Water was added to the reaction mixture, and the mixture was adjusted with an aqueous solution of sodium carbonate to a pH of 9, followed by extraction with ethyl acetate. The organic layer was concentrated under reduced pressure, a the residue obtained was recrystallized from dichloromethane to give 101 mg (0.209 mmol) of N-benzhydryl-N'-[2-{5-(3,4-dihydroxyphenyl)-2,4-pentadienoyl}aminoethyl]piperazine. Spectrophotometric data of the product support the structure shown below. ##STR39##

Workup

  1. temperatureThe mixture was refluxed in an argon atmosphere for 7 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customa the residue obtained
  5. customwas recrystallized from dichloromethane

Sources & evidence

ORD record
ord-926af535096b458d92b07fcb9267e687
Source dataset
uspto-grants-1987_06
Patent number
US04673684

Reaction notes

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