1-Phenylpiperazine → HCID 11592740, compound

HRID 1868590Notes

Reaction equation

HRID 1868590 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:28]=[C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:30]=1)[C:12]1[O:13][C:14]2[C:19]([C:20](=[O:22])[CH:21]=1)=[CH:18][CH:17]=[C:16]([O:23][CH2:24][CH:25]1[O:27][CH2:26]1)[CH:15]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:39]1([N:45]2[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]2)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>CO>[CH2:32]([O:31][C:29]1[CH:28]=[C:11]([CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:30]=1)[C:12]1[O:13][C:14]2[C:19]([C:20](=[O:22])[CH:21]=1)=[CH:18][CH:17]=[C:16]([O:23][CH2:24][CH:25]([OH:27])[CH2:26][N:48]1[CH2:49][CH2:50][N:45]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH2:46][CH2:47]1)[CH:15]=2)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 70961-PhenylpiperazineHCID 76554795HCID 76554795, compound2×

Product 1

HCID 11592740HCID 11592740, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3′,5′-Dibenzyloxy-7-(2,3-epoxy-propoxy)-flavone, 28 (2.5 g, 4.9 mmol) and 1-phenyl piperazine (0.76 mL, 5 mmol) in dry methanol (180 mL) were reacted in a similar manner to that described under 34 to afford 36. Yield 3.1 g (94%); mp 168-170° C.; MS (FAB) 669 (M++1); IR (KBr) 3389, 1634; 1H NMR (200 MHz, CDCl3) δ 8.12 (d, J=8.6 Hz, 1H), 7.46-7.30 (m, 10H), 7.26-7.23 (m, 2H), 7.11 (d, J=1.9 Hz, 2H), 7.00 (d, J=8.5 Hz, 1H), 6.98 (s, 1H), 6.95-6.86 (m, 3H), 6.76 (s, 1H), 6.69 (s, 1H), 5.09 (s, 4H), 4.21-4.14 (m, 3H), 3.23 (t, J=4.7 Hz, 4.6 Hz, 4H), 2.91-2.81 (m, 2H), 2.66 (dd, J=5.2 Hz, 4.1 Hz, 4H). Analysis Calcd for C42H40N2O6: C, 75.43; H, 6.03; N, 4.19. Found: C, 75.37; H, 6.20; N, 4.13.

Sources & evidence

ORD record
ord-e7849c9a424046d38edd4c64c9fc1e27
Source dataset
uspto-grants-2009_12
Patent number
US07635779B2

Reaction notes

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