3,4-Dimethylaniline → (3,4-Dimethyl-phenyl)-[2-(5-trifluoromethyl-pyridin-2-yl)-ethyl]-amine

HRID 1094365ノート

反応式

HRID 1094365 の反応式
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[CH:5][C:6]([CH:9]=[CH2:10])=[N:7][CH:8]=1.[CH3:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][C:20]=1[CH3:21])[NH2:17].O.[OH-].[Cs+]>CN1C(=O)CCC1.C(OCC)(=O)C>[CH3:13][C:14]1[CH:15]=[C:16]([NH:17][CH2:10][CH2:9][C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:11])[F:12])=[CH:8][N:7]=2)[CH:18]=[CH:19][C:20]=1[CH3:21]

参加物

6

反応物 3

HCID 72483,4-DimethylanilineHCID 23679066Caesium hydroxide--water (1/1/1)HCID 589339925-(Trifluoromethyl)-2-vinylpyridine

生成物 1

HCID 58007501(3,4-Dimethyl-phenyl)-[2-(5-trifluoromethyl-pyridin-2-yl)-ethyl]-amine収率 63%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
120 °C

実験手順

A mixture of 200 mg (0.92 mmol) 5-trifluoromethyl-2-vinyl-pyridine (CAS: 204569-89-1), 570 mg (4.62 mmol) 3,4-dimethylaniline and 33 mg (0.18 mmol) cesium hydroxide monohydrate in 2 mL NMP was heated in a 120° C. oil-bath for 22 hours. The mixture was cooled to room temperature and diluted with ethyl acetate. The solution was washed 3 times with water, dried over Na2SO4, filtered and concentrated in vacuo. The crude oil was purified with flash column chromatography on silica eluting with a gradient formed from heptane and ethylacetate to provide 0.17 g (63%) of the title compound as a light yellow oil. MS (m/e): 295.2 [M+H]+.

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. washThe solution was washed 3 times with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude oil was purified with flash column chromatography on silica eluting with a gradient
  7. customformed from heptane and ethylacetate

出典と根拠

ORDレコード
ord-1d95e61e8cd442bf865708c72aa6f22c
出典データセット
uspto-grants-2012_03
特許番号
US08133909B2

反応ノート

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