Methanol → 1-(2-Methoxyphenyl)piperazine

HRID 1157981Notes

Reaction equation

HRID 1157981 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].[CH3:38][OH:39]>>[OH:37][CH:23]([CH2:24][N:25]1[CH2:26][CH2:27][N:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[O:39][CH3:38])[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.[CH3:38][O:39][C:36]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[N:28]1[CH2:27][CH2:26][NH:25][CH2:30][CH2:29]1

Participants

5

Reactant 2

HCID 887MethanolHCID 68643698HCID 68643698, compound

Product 3

HCID 13461-(2-Methoxyphenyl)piperazineHCID 68643663HCID 68643663, compoundHCID 76010298HCID 76010298, compound

Procedure

In a similar manner to the preparation of 18, compound 24 was obtained from 4′-(2,3-epoxy-propoxy)-4-methoxy-chalcone, 13 (500 mg, 1.6 mmol) and 1-(2-methoxyphenyl)piperazine (0.3 mL, 1.7 mmol) in dry methanol (80 mL). Yield 530 mg (66%); mp 97-98° C.; MS (FAB) 503 (M++1); IR (KBr) 3451, 1652; 1H NMR (200 MHz, CDCl3) δ 8.03 (d, J=8.3 Hz, 2H), 7.78 (d, J=15.5 Hz, 1H), 7.60 (d, J=8.1 Hz, 2H), 7.43 (d, J=15.4 Hz, 1H), 7.03-6.85 (m, 8H), 4.13-4.09 (m, 3H), 3.87 (s, 3H), 3.86 (s, 3H), 3.14-3.10 (m, 4H), 2.90-2.88 (m, 2H), 2.67-2.63 (m, 4H). Analyses calculated for C30H34N2O5: C, 71.69; H, 6.82; N, 5.57. Found: C, 71.62; H, 6.91; N, 5.42.

Sources & evidence

ORD record
ord-75777159b2b848439976347d529d895a
Source dataset
uspto-grants-2010_10
Patent number
US07807712B2

Reaction notes

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