1-Phenylpiperazine → HCID 68643698, compound

HRID 1157978Notes

Reaction equation

HRID 1157978 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]3[O:25][CH2:24]3)=[CH:17][CH:16]=2)=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:26]1([N:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]([C:15]2[CH:16]=[CH:17][C:18]([O:21][CH2:22][CH:23]([OH:25])[CH2:24][N:35]3[CH2:36][CH2:37][N:32]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH2:33][CH2:34]3)=[CH:19][CH:20]=2)=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 70961-PhenylpiperazineHCID 86761185HCID 86761185, compound2×

Product 1

HCID 68643698HCID 68643698, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3,4-dimethoxy-4′-(2,3-epoxy-propoxy)-chalcone, 16 (1 g, 2.9 mmol) and 1-phenyl piperazine (0.45 mL, 3 mmol) in dry methanol (90 mL) was stirred at reflux for 6 h. Reaction mixture was concentrated on rotavapor and crude product purified by column chromatography to afford 18. Yield 870 mg (60%); mp 126-127° C.; MS (FAB) 503 (M++1); IR (KBr) 3426, 1652; 1H NMR (200 MHz, CDCl3) δ 8.03 (d, J=8.8 Hz, 2H), 7.76 (d, J=15.5 Hz, 1H), 7.39 (d, J=15.5 Hz, 1H), 7.31-7.20 (m, 3H), 7.16 (d, J=1.3 Hz, 1H), 7.01 (d, J=8.8 Hz, 2H), 6.93 (d, J=7.8 Hz, 1H), 6.95-6.87 (m, 3H), 4.19-4.08 (m, 3H), 3.95 (s, 3H), 3.92 (s, 3H), 3.23 (t, J=4.7 Hz, 4H), 2.90-2.85 (m, 2H), 2.69-2.61 (m, 1H); 13C NMR (50 MHz, CDCl3) δ 189.2, 162.8, 151.8, 151.6, 149.7, 144.6, 132.1, 131.1, 129.6, 128.5, 123.4, 120.3, 116.6, 114.8, 111.7, 110.7, 70.9, 65.9, 60.8, 56.5, 53.8, 49.7. Analyses calculated for C30H34N2O5: C, 71.69; H, 6.82; N, 5.57. Found: C, 71.18; H, 6.93; N, 5.32.

Workup

  1. temperatureat reflux for 6 h
  2. customReaction mixture
  3. concentrationwas concentrated on rotavapor and crude product
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-01bd4452eaf5401eaad3effc6488bef5
Source dataset
uspto-grants-2010_10
Patent number
US07807712B2

Reaction notes

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