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Trifluoroacetic acid → 1-[[4-(2,6-Dimethylpyridin-4-yl)-2-methylphenyl]methyl]piperazine

HRID 2278275
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HRID 2278275 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][N:15]3[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]3)=[C:10]([CH3:28])[CH:9]=2)[CH:5]=[C:4]([CH3:29])[N:3]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:29][C:4]1[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)=[C:10]([CH3:28])[CH:9]=2)[CH:7]=[C:2]([CH3:1])[N:3]=1
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참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 89677209Tert-butyl 4-[[4-(2,6-dimethylpyridin-4-yl)-2-methylphenyl]methyl]piperazine-1-carboxylate

생성물 1

HCID 896769931-[[4-(2,6-Dimethylpyridin-4-yl)-2-methylphenyl]methyl]piperazine수율 103.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A 50 mL round-bottom flask maintained with an inert atmosphere of nitrogen was charged with tert-butyl 4-[[4-(2,6-dimethylpyridin-4-yl)-2-methylphenyl]methyl]piperazine-1-carboxylate (350 mg, 0.880 mmol, 1.00 equiv) and dichloromethane (5 mL). Trifluoroacetic acid (0.5 mL) was added dropwise at 0° C. The resulting solution was stirred for 5 h at room temperature. The reaction progress was monitored by LCMS. The reaction was then quenched by the addition of water (10 mL). The resulting solution was extracted with dichloromethane (3×10 mL) and the organic layers were combined, washed with brine (2×10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to yield 270 mg (crude) of 1-[[4-(2,6-dimethylpyridin-4-yl)-2-methylphenyl]methyl]piperazine as yellow oil. LCMS (ESI, m/z): 296 [M+H]+.

후처리

  1. temperatureA 50 mL round-bottom flask maintained with an inert atmosphere of nitrogen
  2. customThe reaction was then quenched by the addition of water (10 mL)
  3. extractionThe resulting solution was extracted with dichloromethane (3×10 mL)
  4. washwashed with brine (2×10 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-706b08212e6d4d04ba741378008a7792
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09133148B2

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