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

HRID 358761
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HRID 358761 반응식
[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]
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참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b823256a481d4700b5ccad7bb1278d79
출처 데이터셋
uspto-grants-1991_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04997836

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