Sodium Carbonate → N-[3-(3,5-dimethoxy-4-hydroxyphenyl)-2-propenoyl]-N'-(2-benzhydroxyethyl) piperazine

HRID 652966Notes

Reaction equation

HRID 652966 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][O:30][CH:31]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=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.C(=O)([O-])[O-].[Na+].[Na+]>CO.O>[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][O:30][CH:31]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:24][CH2:23]2)=[O:21])[CH:6]=[C:7]([O:16][CH3:17])[C:8]=1[OH:9]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 53756827N-[3[3,5-dimethoxy-4-(beta-methoxyethoxymethoxy)phenyl]-2-propenoyl]-N'-(2-benzhydroxyethyl) piperazine

Product 1

HCID 54574456N-[3-(3,5-dimethoxy-4-hydroxyphenyl)-2-propenoyl]-N'-(2-benzhydroxyethyl) piperazineYield 75%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 588 mg (0.995 mmol) of the amide compound in methanol (10 ml) was added 190 mg (0.999 mmol) of p-toluenesulfonic acid monohydrate, and the mixture was refluxed for 1 hour. The reaction mixture was diluted with water and adjusted to a pH value of 10 by the addition of 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 375 mg (0.746 mmol) of N-[3-(3,5-dimethoxy-4-hydroxyphenyl) -2-propenoyl]-N'-(2-benzhydroxyethyl) piperazine. Spectrophotometric data of the product support the structure shown below. ##STR92##

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-af3e044513204e639d60d3599717b448
Source dataset
uspto-grants-1987_06
Patent number
US04673684

Reaction notes

Loading…