1-Benzoylpiperazine → N-(2-(4-benzoylpiperazin-1-yl)-5-nitrophenyl)benzamide

HRID 1966449Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[NH:11][C:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:20]([N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN1C(=O)CCC1>[C:20]([N:28]1[CH2:33][CH2:32][N:31]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=2[NH:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:30][CH2:29]1)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 125 °C

Procedure

N-(2-bromo-5-nitrophenyl)benzamide (0.3 g, 0.9 mmol) and benzoylpiperazine (0.53 g, 3.00 mmol) were dissolved in 15 NMP and heated at 125° C. for 16 hours. The reaction was quenched with 100 ml water after cooling to room temperature. The mixture was extracted with 50 ml acetyl acetate and washed by water (3×20 ml). N-(2-(4-benzoylpiperazin-1-yl)-5-nitrophenyl)benzamide (0.20 g, 50%) was obtained after flash column chromatograph (50% ethyl acetate in hexanes). 1H NMR (500 MHz, CDCl3) δ (ppm) 3.06 (s, br, 4H), 3.85 (d, br, 4H), 7.31 (d, J=8.8 Hz, 1H), 7.48 (m, 5H), 7.62 (m, 2H), 7.65 (m, 1H), 7.95 (d, J=7.1 Hz, 2H), 8.06 (dd, J=2.6, 8.8 Hz, 1H), 9.12 (s, 1H), 9.47 (d, J=2.6 Hz, 1H). 13C NMR (125 MHz, CDCl3): δ (ppm) 52.4, 115.9, 119.9, 121.0, 127.3, 127.6, 129.2, 129.7, 130.7, 133.0, 134.2, 134.5, 135.5, 145.9, 146.7, 165.3, 171.2.

Workup

customThe reaction was quenched with 100 ml water
temperatureafter cooling to room temperature
extractionThe mixture was extracted with 50 ml acetyl acetate
washwashed by water (3×20 ml)

Sources & evidence

ORD record: ord-6acb6f0c85e34b2bbc6eb6c957341d9d
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420640B2

Reaction notes

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