Water → HCID 19972395, compound

HRID 2259911Notes

Reaction equation

HRID 2259911 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([C:8]1[C:17]2[O:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:14]([CH3:24])[C:13](=[O:25])[C:12]=2[CH:11]=[CH:10][CH:9]=1)(=[O:7])=[O:6].[CH3:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1.O>CN(C)C=O>[ClH:1].[CH3:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[N:34]1[CH2:39][CH2:38][N:37]([CH2:2][CH2:3][CH2:4][S:5]([C:8]2[C:17]3[O:16][C:15]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[C:14]([CH3:24])[C:13](=[O:25])[C:12]=3[CH:11]=[CH:10][CH:9]=2)(=[O:7])=[O:6])[CH2:36][CH2:35]1

Participants

5

Reactant 3

HCID 962WaterHCID 13461-(2-Methoxyphenyl)piperazineHCID 19972358HCID 19972358, compound

Product 1

HCID 19972395HCID 19972395, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3.8 g of Intermediate XXXV and 4 g of 1-(2-methoxyphenyl)-piperazine in 40 ml of dimethylformamide was heated at 60° C. for 7 hours. After cooling to 20°-25° C., the reaction mixture was poured into 500 ml of water and extracted with dichloromethane. The organic extracts were washed with water and dried on anhydrous sodium sulfate, and the solvent was then evaporated off in vacuo. The residue was purified by flash chromatography on silica gel, eluting with ethyl acetate:petroleum ether (1:1). The base of the title compound was obtained. It was dissolved in ethanol and one equivalent of ethanolic hydrogen chloride was added to give 4.5 g of the title compound, m.p. (215) 226°-228C.

Workup

  1. temperatureAfter cooling to 20°-25° C.
  2. extractionextracted with dichloromethane
  3. washThe organic extracts were washed with water
  4. dry with materialdried on anhydrous sodium sulfate
  5. customthe solvent was then evaporated off in vacuo
  6. customThe residue was purified by flash chromatography on silica gel
  7. washeluting with ethyl acetate:petroleum ether (1:1)

Sources & evidence

ORD record
ord-87bb0e3c53624a0bab68cbadc2456d3b
Source dataset
uspto-grants-1995_12
Patent number
US05474994

Reaction notes

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