1-Phenylpiperazine → 1-[(3-Methoxy-6-methylquinoxalin-2-yl)aminocarbonyl]-4-phenylpiperazine

HRID 1878232Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:4]([NH:14][C:15](=[O:19])OCC)=[N:5][C:6]2[C:11]([N:12]=1)=[CH:10][C:9]([CH3:13])=[CH:8][CH:7]=2.[C:20]1([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C1CCN2C(=NCCC2)CC1>O1CCCC1>[CH3:1][O:2][C:3]1[C:4]([NH:14][C:15]([N:29]2[CH2:30][CH2:31][N:26]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:27][CH2:28]2)=[O:19])=[N:5][C:6]2[C:11]([N:12]=1)=[CH:10][C:9]([CH3:13])=[CH:8][CH:7]=2

Participants

Conditions

Temperature: 70 °C

Procedure

Ethyl N-(3-methoxy-6-methylquinoxalin-2-yl)carbamate (30 mg, 0.11 mmol) and 1-phenylpiperazine (24 mg, 0.15 mmol) were dissolved in tetrahydrofuran (2 ml) at room temperature and thereto DBU (23 mg, 0.15 mmol) was added. The resulting mixture was stirred at 70° C. for 7 hours and concentrated under the reduced pressure to remove the solvent, and purified by SiO2 column chromatography. Extraction of the residue with a n-hexane:ethyl acetate (2:1) mixture and concentration gave 34 mg of the titled compound (yield, 90%). 1H NMR (300 MHz, CDCl3): δ 2.43 (s, 3H), 3.22-3.29 (m, 4H), 3.73-3.87 (m, 4H), 4.13 (s, 3H), 6.87-7.74 (m, 9H).

Workup

concentrationconcentrated under the reduced pressure
customto remove the solvent
custompurified by SiO2 column chromatography
extractionExtraction of the residue
concentrationwith a n-hexane:ethyl acetate (2:1) mixture and concentration

Sources & evidence

ORD record: ord-ca6b8969650a45819040b3ad5d54d5ca
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314100B2

Reaction notes

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