Water → HCID 19972356, compound

HRID 1452304Notes

Reaction equation

HRID 1452304 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].C([O-])(=O)C.[Na+].Cl[CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][CH3:34])[CH2:23][CH2:22]1.O>CS(C)=O>[O:7]=[C:6]1[C:5]2[C:4](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3](=[O:12])[N:2]1[O:1][CH2:19][CH2:20][N:21]1[CH2:22][CH2:23][N:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][CH3:34])[CH2:25][CH2:26]1

Participants

6

Reactant 4

HCID 962WaterHCID 10665N-HydroxyphthalimideHCID 517045Sodium AcetateHCID 5956731-(2-Chloroethyl)-4-(2-methoxyphenyl)piperazine

Product 1

HCID 19972356HCID 19972356, compoundYield 50.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6.73 g of N-hydroxyphthalimide, 3.73 g of sodium acetate and 10 g of 1-(2-chloroethyl)-4-(2-methoxyphenyl)piperazine in 100 ml of anhydrous dimethylsulfoxide was stirred at 100° C. for 4 hours. The reaction mixture was then cooled to room temperature, poured into water and extracted with ethyl acetate. The collected organic layers were washed with 1N aqueous sodium hydroxide solution, dried on anhydrous sodium sulfate and evaporated to dryness in vacuo to give 7.58 g of the title compound. A sample was crystallized from cyclohexane, m.p. (76) 80°-83° C.

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe collected organic layers were washed with 1N aqueous sodium hydroxide solution
  4. dry with materialdried on anhydrous sodium sulfate
  5. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-ca41e07423a144dbb617fe0d951c8227
Source dataset
uspto-grants-1997_02
Patent number
US05605896

Reaction notes

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