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

HRID 358760
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HRID 358760 반응식
Cl.Cl.[NH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH:4]1[C:9]([O:11][CH2:12][CH3:13])=[O:10].C(N(CC)CC)C.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:29]=[C:30]([O:34][CH3:35])[C:31]=1[O:32][CH3:33])[C:26](Cl)=[O:27]>ClCCl>[CH3:35][O:34][C:30]1[CH:29]=[C:25]([CH:24]=[C:23]([O:22][CH3:21])[C:31]=1[O:32][CH3:33])[C:26]([N:6]1[CH2:7][CH2:8][NH:3][CH:4]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5]1)=[O:27]
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 11253230Ethyl Piperazine-2-carboxylate Dihydrochloride

생성물 1

HCID 10360649Ethyl 4-(3,4,5-trimethoxybenzoyl)piperazine-2-carboxylate수율 88.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a mixture of ethyl piperazine-2-carboxylate dihydrochloride (2.0 g), triethylamine (1.2 ml) and dichloromethane (40 ml) is added dropwise, under ice-cooling while stirring, a solution of 3,4,5-trimethoxybenzoyl chloride (1.85 g) in dichloromethane (25 ml). The mixture is stirred for one hour, then the reaction mixture is poured into ice-water, followed by extraction with methylene chloride. The organic layer is washed with water, dried and concentrated under reduced pressure. The residue is purified by means of a silica gel column chromatography (eluent : ethyl acetate-acetone-hexane=2:1:2) to afford ethyl 4-(3,4,5-trimethoxybenzoyl)piperazine-2-carboxylate (2.5 g). This product is recrystallized from ethyl acetatehexane to give colorless crystals, m.p. 114-115° C.

후처리

  1. additionis added dropwise, under ice-
  2. temperaturecooling
  3. stirringThe mixture is stirred for one hour
  4. extractionfollowed by extraction with methylene chloride
  5. washThe organic layer is washed with water
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified by means of a silica gel column chromatography (eluent : ethyl acetate-acetone-hexane=2:1:2)

출처 및 근거

ORD 기록
ord-ec85f6572af341008f26cb694c5b2f6b
출처 데이터셋
uspto-grants-1991_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04997836

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