Toluene → (R)-1-(4-fluoro-2-(trifluoromethyl)phenyl)-3-methylpiperazine

HRID 1868126

반응식

HRID 1868126 반응식
[CH3:1][C@@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][NH:3]1.[F:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=1.CC(C)([O-])C.[Na+].C1(C)C=CC=CC=1>ClCCl.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:8][C:9]1[CH:10]=[CH:11][C:12]([N:6]2[CH2:5][CH2:4][NH:3][C@H:2]([CH3:1])[CH2:7]2)=[C:13]([C:15]([F:16])([F:17])[F:18])[CH:14]=1

참가 물질

7

반응물 4

HCID 1140TolueneHCID 67867alpha,alpha,alpha,3-TetrafluorotolueneHCID 73304342-Methylpiperazine, (R)-HCID 23676156Sodium t-butoxide

생성물 1

HCID 68554948(R)-1-(4-fluoro-2-(trifluoromethyl)phenyl)-3-methylpiperazine수율 33.6%

시약·촉매·용매 2

HCID 634876Binap, (A+-)-촉매HCID 6344Dichloromethane용매

반응 조건

온도
110 °C

실험 절차

(R)-2-methyl-piperazine (3.88 g, 38.70 mmol), 2-bromo, 5-fluoro benzotrifluoride (8.55 g, 35.18 mmol), tris(dibenzylidineacetone)dipalladium (0) (32.0 mg g, 0.35 mmol), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (657.0 mg, 1.06 mmol) and sodium tert-butoxide (5.07 g, 52.77 mmol) were charged to a reaction flask. Toluene (40 mL) was introduced under nitrogen atmosphere and the reaction mixture was heated up at 110° C. for 5.0 hours. Reaction was complete as determined by TLC. The reaction mixture was diluted with dichloromethane, washed with water, saturated brine then dried over MgSO4 and concentrated. The crude product was purified via flash column chromatography to yield (R)-1-(4-fluoro-2-(trifluoromethyl)phenyl)-3-methylpiperazine as a light brown oil (3.1 g, 33.6% yield).

후처리

  1. customReaction
  2. washwashed with water, saturated brine
  3. dry with materialthen dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified via flash column chromatography

출처 및 근거

ORD 기록
ord-9fadd48193674f86aee2834e1273fc9f
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07632838B2

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