HCID 68643698, compound → 1-Phenylpiperazine

HRID 1157983Notes

Reaction equation

HRID 1157983 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH:23]([OH:37])[CH2:24][N:25]3[CH2:30][CH2:29][N:28]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH2:27][CH2:26]3)=[CH:17][CH:16]=2)=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]>CO>[OH:37][CH:23]([CH2:24][N:25]1[CH2:30][CH2:29][N:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:27][CH2:26]1)[CH2:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([C:13](=[O:14])[CH:12]=[CH:11][C:5]2[CH:6]=[CH:7][C:8]3[O:9][CH2:10][O:2][C:3]=3[CH:4]=2)=[CH:16][CH:17]=1.[O:37]1[CH2:24][CH:23]1[CH2:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([C:13](=[O:14])[CH:12]=[CH:11][C:5]2[CH:6]=[CH:7][C:8]3[O:9][CH2:1][O:2][C:3]=3[CH:4]=2)=[CH:16][CH:17]=1.[C:31]1([N:28]2[CH2:29][CH2:30][NH:25][CH2:26][CH2:27]2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 1

HCID 68643698HCID 68643698, compound

Product 3

HCID 70961-PhenylpiperazineHCID 68643658HCID 68643658, compoundHCID 91507293HCID 91507293, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a similar manner to the preparation of 18, compound 33 was obtained from 4′-(2,3-epoxy-propoxy)-3,4-methylenedioxy-chalcone, 17 (500 mg, 1.5 mmol) and 1-phenyl piperazine (0.23 mL, 1.5 mmol) in dry methanol (60 mL). Yield 540 mg (72%); mp 153-154° C.; MS (FAB) 487 (M++1); IR (KBr) 3396, 1651; 1H NMR (200 MHz, CDCl3) δ 8.02 (d, J=8.8 Hz, 2H), 7.71 (d, J=15.5 Hz, 1H), 7.38 (d, J=15.5 Hz, 1H), 7.27 (t, J=7.9 Hz, 2H), 7.16 (s, 1H), 7.12 (d, J=8.0 Hz, 1H), 7.01 (d, J=8.8 Hz, 2H), 6.97 (d, J=7.2 Hz, 1H), 6.91-6.82 (m, 3H), 6.02 (s, 2H), 4.17-4.09 (m, 3H), 3.23 (t, J=4.8 Hz, 4H), 2.89-2.81 (m, 2H), 2.69-2.62 (m, 4H). Analyses calculated for C29H30N2O5: C, 71.59; H, 6.21; N, 5.76. Found: C, 71.62; H, 6.30; N, 5.81.

Sources & evidence

ORD record
ord-27fd3d6fe0c7481aa1b8c74d255d5b71
Source dataset
uspto-grants-2010_10
Patent number
US07807712B2

Reaction notes

Loading…