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Triethylamine → 1-(Benzyloxycarbonyl)-3-(2,3-dimethoxybenzyl)piperazine

HRID 584218
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HRID 584218 반응식
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:12][O:13][C:14]1[C:26]([O:27][CH3:28])=[CH:25][CH:24]=[CH:23][C:15]=1[CH2:16][CH:17]1[CH2:22][NH:21][CH2:20][CH2:19][NH:18]1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>ClCCl.O>[CH2:1]([O:8][C:9]([N:21]1[CH2:20][CH2:19][NH:18][CH:17]([CH2:16][C:15]2[CH:23]=[CH:24][CH:25]=[C:26]([O:27][CH3:28])[C:14]=2[O:13][CH3:12])[CH2:22]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 22342949HCID 22342949, 화합물

생성물 1

HCID 223427101-(Benzyloxycarbonyl)-3-(2,3-dimethoxybenzyl)piperazine수율 53.1%

시약·촉매·용매 2

HCID 962Water용매
HCID 6344Dichloromethane용매3회

실험 절차

A solution of benzyloxycarbonyl chloride (0.59 g) in dichloromethane (3.0 ml) was added dropwise to a solution of 2-(2,3-dimethoxybenzyl)piperazine (0.91 g) and triethylamine (0.64 ml) in dichloromethane (18 ml) below 5° C. over 5 minutes under ice-cooling, and the reaction mixture was stirred at the same temperature for 15 minutes. After 2 hours of stirring at room temperature, the mixture was poured into a mixed solvent of water (40 ml) and dichloromethane (25 ml) and the whole was adjusted to pH 9 with aqueous sodium hydrogen carbonate solution. The organic layer was separated, washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (20 g) using a mixed solvent of dichloromethane and methanol (40:1). The fractions containing the objective compound were collected and evaporated under reduced pressure to give colorless oil of 1-(benzyloxycarbonyl)-3-(2,3-dimethoxybenzyl)piperazine (0.68 g).

후처리

  1. temperaturecooling
  2. stirringAfter 2 hours of stirring at room temperature
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (20 g)
  8. additionThe fractions containing the objective compound
  9. customwere collected
  10. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-328a69c68dc94231a7094a2e031bd54d
출처 데이터셋
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06924278B2

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