Water → HCID 18408778, compound

HRID 1872560Notes

Reaction equation

HRID 1872560 reaction equation
Br[C:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[OH:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.O>CS(C)=O>[C:13]1([C:2]([N:25]2[CH2:26][CH2:27][N:22]([CH2:21][CH2:20][OH:19])[CH2:23][CH2:24]2)([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 76771-(2-Hydroxyethyl)piperazineHCID 12491978HCID 12491978, compound

Product 1

HCID 18408778HCID 18408778, compoundYield 33.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of diethyl 2-bromo-2-phenylmalonate (16.8 g) in 150 ml of dimethylsulfoxide is heated to 90-100° C., then N-(2-hydroxyethyl)piperazine (27.9 g) is added and the reaction mixture is heated for additional 4 hours. The mixture is poured into water and extracted with ethyl acetate three times. The pooled organic extracts are washed with 1 N hydrochloric acid. The aqueous phase is basified with 1 N sodium hydroxide to pH=8-9 and it is extracted twice with ethyl acetate. The organic extracts are collected and are washed with a saturated aqueous solution of sodium chloride and dried over sodium sulfate. After removal of the solvent under reduced pressure, the residue is crystallized from diethylether petroleum ether 1:1 to give 6.5 g of the product, m.p. 63-64° C.

Workup

  1. temperaturethe reaction mixture is heated for additional 4 hours
  2. extractionextracted with ethyl acetate three times
  3. washThe pooled organic extracts are washed with 1 N hydrochloric acid
  4. extractionis extracted twice with ethyl acetate
  5. customThe organic extracts are collected
  6. washare washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over sodium sulfate
  8. customAfter removal of the solvent under reduced pressure
  9. customthe residue is crystallized from diethylether petroleum ether 1:1

Sources & evidence

ORD record
ord-6a04a6290e0242a1b117d9feac58f727
Source dataset
uspto-grants-2000_08
Patent number
US06110924

Reaction notes

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