1-Phenylpiperazine → HCID 11671153, compound

HRID 1868596Notes

Reaction equation

HRID 1868596 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26])[C:6]1[O:7][C:8]2[C:13]([C:14](=[O:16])[CH:15]=1)=[CH:12][CH:11]=[C:10]([O:17][CH2:18][CH:19]1[O:21][CH2:20]1)[CH:9]=2.[C:29]1([N:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CO>[OH:21][CH:19]([CH2:20][N:38]1[CH2:39][CH2:40][N:35]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:36][CH2:37]1)[CH2:18][O:17][C:10]1[CH:9]=[C:8]2[C:13]([C:14](=[O:16])[CH:15]=[C:6]([C:5]3[CH:22]=[C:23]([O:27][CH3:28])[C:24]([O:25][CH3:26])=[C:3]([O:2][CH3:1])[CH:4]=3)[O:7]2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 70961-PhenylpiperazineHCID 86606987HCID 86606987, compound2×

Product 1

HCID 11671153HCID 11671153, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3′,4′,5′-Trimethoxy-7-(2,3-epoxy-propoxy)-flavone, 31 (1.1 g, 3 mmol) and 1-phenyl piperazine (0.5 mL, 3.27 mmol) in dry methanol (130 mL) were reacted in a similar manner to that described under 34 to afford 42. Yield 1.4 g (85%); mp 170-171° C.; MS (FAB) 547 (M++1); IR (KBr) 3406, 1635; 1H NMR (200 MHz, CDCl3) δ 8.13 (d, J=9.5 Hz, 1H), 7.27 (t, J=7.9 Hz, 2H), 7.10 (s, 2H), 7.04-7.01 (m, 2H), 6.95-6.87 (m, 3H), 6.70 (s, 1H), 4.21-4.12 (m, 3H), 3.95 (s, 6H), 3.93 (s, 3H), 3.23 (t, J=4.6 Hz, 4H), 2.87-2.83 (m, 2H), 2.68-2.65 (m, 4H). Analysis Calcd for C31H34N2O7: C, 68.12; H, 6.27; N, 5.12. Found: C, 68.26; H, 6.37; N, 5.41.

Sources & evidence

ORD record
ord-2702558479334ac8bbc6ee675d4390b3
Source dataset
uspto-grants-2009_12
Patent number
US07635779B2

Reaction notes

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