Triethylamine → Methyl 4-(3,4,5-trimethoxybenzoyl)piperazine-2-carboxylate

HRID 358761Notes

Reaction equation

HRID 358761 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6](Cl)=[O:7].Cl.Cl.[NH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH:19]1[C:24]([O:26][CH3:27])=[O:25].C(N(CC)CC)C>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6]([N:21]1[CH2:22][CH2:23][NH:18][CH:19]([C:24]([O:26][CH3:27])=[O:25])[CH2:20]1)=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 2760425Methyl Piperazine-2-carboxylate Dihydrochloride

Product 1

HCID 20066647Methyl 4-(3,4,5-trimethoxybenzoyl)piperazine-2-carboxylateYield 60.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3,4,5-trimethoxybenzoyl chloride (10.9 g) in dichloromethane (100 ml) is added dropwise taking one hour, under ice-cooling while stirring, to a mixture of methyl piperazine-2-carboxylate dihydrochloride (10.24 g), triethylamine (18.7 g) and dichloromethane (200 ml). The reaction mixture is poured into ice-water, followed by extraction with dichloromethane. The organic layer is washed with water, dried and the solvent is distilled off under reduced pressure. Crystals obtained from the residue are recrystallized from ethyl acetate and hexane to afford methyl 4-(3,4,5-trimethoxybenzoyl)piperazine-2-carboxylate (9.6 g) as colorless needles, m.p. 113-114° C.

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with dichloromethane
  3. washThe organic layer is washed with water
  4. customdried
  5. distillationthe solvent is distilled off under reduced pressure
  6. customCrystals obtained from the residue
  7. customare recrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-b823256a481d4700b5ccad7bb1278d79
Source dataset
uspto-grants-1991_03
Patent number
US04997836

Reaction notes

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