1-Phenylpiperazine → HCID 10390156, compound

HRID 1885223Notes

Reaction equation

HRID 1885223 reaction equation
I[CH2:2][CH2:3][S:4][CH:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][O:8][C:7]2[CH:16]=[CH:17][C:18]([C:20]([O:22][CH3:23])=[O:21])=[CH:19][C:6]1=2.[C:24]1([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(O)C>[C:24]1([N:30]2[CH2:35][CH2:34][N:33]([CH2:2][CH2:3][S:4][CH:5]3[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[CH2:9][O:8][C:7]4[CH:16]=[CH:17][C:18]([C:20]([O:22][CH3:23])=[O:21])=[CH:19][C:6]3=4)[CH2:32][CH2:31]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 70961-PhenylpiperazineHCID 10094761HCID 10094761, compound

Product 1

HCID 10390156HCID 10390156, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

After 6.1 g of Compound j obtained in Reference Example 10 and 6.0 ml of 1-phenylpiperazine were heated under reflux in 300 ml of ethanol for 7.5 hours, the solvent was distilled off under reduced pressure. The residue was extracted with 500 ml of ethyl acetate. The extract was washed in succession with saturated sodium bicarbonate aqueous solution and saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled off under reduced pressure. The obtained residue was subjected to silica gel column chromatography (eluent; hexane:ethyl acetate: triethylamine=30:10:3). The resulting crude product was solidified with diethyl ether to give 3.1 g of the objective compound.

Workup

  1. temperaturewere heated
  2. distillationthe solvent was distilled off under reduced pressure
  3. extractionThe residue was extracted with 500 ml of ethyl acetate
  4. washThe extract was washed in succession with saturated sodium bicarbonate aqueous solution and saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThereafter, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-86be7d7380754122b5fd177cc185249a
Source dataset
uspto-grants-1992_09
Patent number
US05143922

Reaction notes

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