1-Phenylpiperazine → HCID 11606012, compound

HRID 1868599Notes

Reaction equation

HRID 1868599 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([O:25][CH3:26])[CH:24]=1)[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:27]1([N:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([O:25][CH3:26])[CH:24]=1)[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]([OH:21])[CH2:20][N:36]1[CH2:37][CH2:38][N:33]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:34][CH2:35]1)[CH:9]=2

Participants

4

Reactant 2

HCID 70961-PhenylpiperazineHCID 86236608HCID 86236608, compound2×

Product 1

HCID 11606012HCID 11606012, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3′,5′-Dimethoxy-7-(2,3-epoxy-propoxy)-flavone, 32 (400 mg, 1.13 mmol) and 1-phenyl piperazine (0.17 mL, 1.13 mmol) in dry methanol (100 mL) were reacted in a similar manner to that described under 34 to afford 45. Yield 490 mg (84%); mp 195-196° C.; MS (FAB) 517 (M++1); IR (KBr) 3417, 1633; 1H NMR (200 MHz, DMSO-d6) δ 7.97 (d, J=8.8 Hz, 1H), 7.40 (d, J=1.9 Hz, 1H), 7.24 (d, J=1.9 Hz (d, J=7.9 Hz, 2H), 7.12 (dd, J=8.9 Hz, 1.9 Hz, 1H), 7.04 (s, 1H), 6.93 (d, J=8.2 Hz, 2H), 6.80 (d, J=7.1 Hz, 1H), 6.74 (s, 1H), 4.25-4.09 (m, 3H), 3.87 (s, 6H), 3.13 (t, J=6.5 Hz, 4H), 2.63 (d, J=4.5 Hz, 2H), 2.47-2.43 (m, 4H). Analysis Calcd for C30H32N2O6: C, 69.75; H, 6.24; N, 5.42. Found: C, 69.61; H, 6.53; N, 5.61.

Sources & evidence

ORD record
ord-ea229ef5ab6444fab372130f035d023e
Source dataset
uspto-grants-2009_12
Patent number
US07635779B2

Reaction notes

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