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Triethylamine → trans-2-[4-(6-Trifluoromethyl-benzo[b]thiophen-3-yl)-piperazin-1-ylmethyl]-cyclopropanecarboxylic Acid Methyl Ester

HRID 1986960
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HRID 1986960 반응식
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[CH:5][C:6]2[C:10]([N:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)=[CH:9][S:8][C:7]=2[CH:17]=1.[CH3:20][O:21][C:22]([C@@H:24]1[CH2:26][C@H:25]1[CH2:27]OS(C)(=O)=O)=[O:23].C(N(CC)CC)C>C(#N)C>[CH3:20][O:21][C:22]([C@@H:24]1[CH2:26][C@H:25]1[CH2:27][N:14]1[CH2:13][CH2:12][N:11]([C:10]2[C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:18])([F:1])[F:19])=[CH:17][C:7]=3[S:8][CH:9]=2)[CH2:16][CH2:15]1)=[O:23]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 112891551-(6-Trifluoromethyl-benzo[b]thiophen-3-yl)-piperazineHCID 86591119trans-2-Methanesulfonyloxymethyl-cyclopropanecarboxylic acid methyl ester

생성물 1

HCID 68456225trans-2-[4-(6-Trifluoromethyl-benzo[b]thiophen-3-yl)-piperazin-1-ylmethyl]-cyclopropanecarboxylic Acid Methyl Ester

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매

실험 절차

Heat at reflux for 16 h, a mixture of 1-(6-trifluoromethyl-benzo[b]thiophen-3-yl)-piperazine, free base of Example 2b, (23.0 g, 71.3 mmol), trans-2-methanesulfonyloxymethyl-cyclopropanecarboxylic acid methyl ester (Example 5a) (15.3 g, 73.5 mmol), and triethylamine (40 mL, 288 mmol) in acetonitrile (600 mL). Concentrate the reaction mixture under reduced pressure and dilute the resultant oil with EtOAc (30 mL). Filter the resulting precipitate (unreacted starting piperazine) away and purify the filtrate by column chromatography over silica gel (EtOAc/heptane/MeOH/triethylamine, 20:20:1). Concentration of the appropriate fractions gives 18.0 g of colorless oil, m/z=413 (M+H)+.

후처리

  1. temperatureHeat
  2. temperatureat reflux for 16 h
  3. concentrationConcentrate the reaction mixture under reduced pressure
  4. additiondilute the resultant oil with EtOAc (30 mL)
  5. filtrationFilter the resulting precipitate (unreacted starting piperazine) away
  6. custompurify the filtrate by column chromatography over silica gel (EtOAc/heptane/MeOH/triethylamine, 20:20:1)

출처 및 근거

ORD 기록
ord-6953ab1b9f31419889ad55f6703572d4
출처 데이터셋
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07550469B2

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