1-Phenylpiperazine → HCID 69961743, compound

HRID 1291409Notes

Reaction equation

Cl[C:2]1[CH:30]=[CH:29][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]=[CH:15][C:16]3[N:25]([CH3:26])[C:24](=[O:27])[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][C:22]=4[CH3:28])[N:17]=3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][N:3]=1.[C:31]1([N:37]2[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>N1C=CC=CC=1>[CH3:26][N:25]1[C:24](=[O:27])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][C:22]=2[CH3:28])[N:17]=[C:16]1[CH:15]=[CH:14][C:11]1[CH:12]=[CH:13][C:8]([C:6](=[O:7])[C:5]2[CH:29]=[CH:30][C:2]([N:40]3[CH2:41][CH2:42][N:37]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH2:38][CH2:39]3)=[N:3][CH:4]=2)=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 2-[2-[4-(6-chloronicotinoyl)-phenyl]vinyl]-3,5-dimethyl-4(3H)-quinazolinone (333 mg) in pyridine (5 ml) was added 1-phenylpiperazine (156 ml) and the mixture was stirred at 90° C. for 4 hours. This reaction mixture was concentrated and extracted with ethyl acetate. The organic layer was washed serially with water and saturated aqueous NaCl solution, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (n-hexane: ethyl acetate (1:1)) to provide 162 mg of yellow powder.

Workup

concentrationThis reaction mixture was concentrated
extractionextracted with ethyl acetate
washThe organic layer was washed serially with water and saturated aqueous NaCl solution
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated
customThe residue was purified by silica gel column chromatography (n-hexane: ethyl acetate (1:1))

Sources & evidence

ORD record: ord-8c20dee825304c92bf7d4d865ef9d496
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05753664

Reaction notes

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