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

HRID 1868126

反応式

HRID 1868126 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 634876Binap, (A+-)-触媒HCID 6344Dichloromethane溶媒

反応条件

温度
110 °C

実験手順

(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).

後処理

  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

出典と根拠

ORDレコード
ord-9fadd48193674f86aee2834e1273fc9f
出典データセット
uspto-grants-2009_12
特許番号
US07632838B2

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