Water → Methyl 4-(4-methoxycinnamoyl)-1(3,4,5-trimethoxybenzoyl)piperazine-2-carboxylate

HRID 358779Notes

Reaction equation

HRID 358779 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9](Cl)=[O:10])=[CH:5][CH:4]=1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:31]=[C:32]([O:36][CH3:37])[C:33]=1[O:34][CH3:35])[C:19]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH:22]1[C:27]([O:29][CH3:30])=[O:28])=[O:20].C(N(CC)CC)C.O>ClCCl>[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9]([N:24]2[CH2:25][CH2:26][N:21]([C:19](=[O:20])[C:18]3[CH:17]=[C:16]([O:15][CH3:14])[C:33]([O:34][CH3:35])=[C:32]([O:36][CH3:37])[CH:31]=3)[CH:22]([C:27]([O:29][CH3:30])=[O:28])[CH2:23]2)=[O:10])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 20066654Methyl 1-(3,4,5-trimethoxybenzoyl)piperazine-2-carboxylateHCID 534017724-Methoxycinnamic acid chloride

Product 1

HCID 53878437Methyl 4-(4-methoxycinnamoyl)-1(3,4,5-trimethoxybenzoyl)piperazine-2-carboxylateYield 78.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-methoxy cinnamoyl chloride (0.3 g) in dichloromethane (4 ml) is added dropwise, taking 3 minutes at 0 ° C while stirring, to a mixture of methyl 1-(3,4,5-trimethoxybenzoyl)piperazine-2-carboxylate (0.57 g), triethylamine (0.4 g) and dichloromethane (12 ml). The reaction mixture is stirred for 30 minutes at room temperature, and then poured into water, followed by extraction with dichloromethane. The organic layer is washed with dilute hydrochloric acid, an aqueous solution of sodium hydrogencarbonate and water, successively, then the solvent is distilled off. The residue is purified by means of a silica gel column chromatography to give methyl 4-(4-methoxycinnamoyl)-1(3,4,5-trimethoxybenzoyl)piperazine-2-carboxylate (0.6 g) as a colorless oily product. This product is processed with ethyl ether to give colorless powder

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. washThe organic layer is washed with dilute hydrochloric acid
  3. distillationan aqueous solution of sodium hydrogencarbonate and water, successively, then the solvent is distilled off
  4. customThe residue is purified by means of a silica gel column chromatography

Sources & evidence

ORD record
ord-c6b2a9131e5340c2968dee10804eb67d
Source dataset
uspto-grants-1991_03
Patent number
US04997836

Reaction notes

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