HCID 68643698, compound → 1-Phenylpiperazine

HRID 1157979Notes

Reaction equation

HRID 1157979 reaction equation
CO[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[CH2:26][CH2:27][N:28]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:29][CH2:30]1)[CH2:22][O:21][C:18]1[CH:17]=[CH:16][C:15]([C:13](=[O:14])[CH:12]=[CH:11][C:5]2[CH:4]=[CH:3][C:8]([O:9][CH3:10])=[CH:7][CH:6]=2)=[CH:20][CH:19]=1.[O:37]1[CH2:24][CH:23]1[CH2:22][O:21][C:18]1[CH:17]=[CH:16][C:15]([C:13](=[O:14])[CH:12]=[CH:11][C:5]2[CH:4]=[CH:3][C:8]([O:9][CH3:10])=[CH:7][CH:6]=2)=[CH:20][CH:19]=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 215794HCID 215794, compoundHCID 76010298HCID 76010298, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a similar manner to the preparation of 18, compound 20 was obtained from 4′-(2,3-epoxy-propoxy)-4-methoxy-chalcone, 13 (1.3 g, 4.2 mmol) and 1-phenyl piperazine (0.64 mL, 4.2 mmol) in dry methanol (120 mL). Yield 1.4 g (70%); mp 165-167° C.; MS (FAB) 473 (M++1); IR (KBr) 3392, 1652; 1H NMR (200 MHz, CDCl3) δ 8.03 (d, J=8.8 Hz, 2H), 7.78 (d, J=15.6 Hz, 1H), 7.60 (d, J=8.6 Hz, 2H), 7.42 (d, J=15.5 Hz, 1H), 7.31-7.24 (m, 2H), 7.01 (d, J=8.7 Hz, 2H), 6.94 (d, J=8.7 Hz, 2H), 6.96-6.84 (m, 3H), 4.19-4.09 (m, 3H), 3.86 (s, 3H), 3.24 (t, J=4.9 Hz, 4H), 2.89-2.84 (m, 2H), 2.74-2.64 (m, 4H). Analyses calculated for C29H32N2O4: C, 73.70; H, 6.83; N, 5.93. Found: C, 73.32; H, 6.41; N, 5.69.

Sources & evidence

ORD record
ord-b46a9ffcf52b4ee3bac304dd2772ad02
Source dataset
uspto-grants-2010_10
Patent number
US07807712B2

Reaction notes

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