Acetonitrile → 1-benzhydryl-N-(4-fluorophenyl)azetidin-3-amine

HRID 72402

反応式

HRID 72402 の反応式
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C(#N)C.CS(O[CH:17]1[CH2:20][N:19]([CH:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:18]1)(=O)=O>>[CH:21]([N:19]1[CH2:20][CH:17]([NH:6][C:5]2[CH:7]=[CH:8][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:18]1)([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

参加物

4

反応物 3

HCID 6342AcetonitrileHCID 97314-FluoroanilineHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonate

生成物 1

HCID 679582291-benzhydryl-N-(4-fluorophenyl)azetidin-3-amine

反応条件

温度
100 °C

実験手順

To a solution of 4-fluoro aniline (0.412 ml, 4.296 mmol) in acetonitrile (10 ml) potassium carbonate (771 mg, 5.584 mmol) was added followed by addition of 1-benzhydrylazetidin-3-yl methanesulfonate (D19) (1.5 g, 4.72 mmol). The reaction mixture was stirred at 100° C. for 5 minutes under microwave irradiation. Solvents were evaporated under vacuo and the residue was taken in with diethylether (50 ml) then water (50 ml) was added. The aqueous layer was extracted with diethylether (2×30 ml). The organics after solvent evaporation were purified by Biotage SNAP-Si cartridge (25 g) eluting with cyclohexane/ethylacetate from 100-0 to 85/15. Collected fractions, after solvent evaporation afforded the title (D24) (0.5 g)

後処理

  1. customSolvents were evaporated under vacuo
  2. additionwater (50 ml) was added
  3. extractionThe aqueous layer was extracted with diethylether (2×30 ml)
  4. customThe organics after solvent evaporation
  5. customwere purified by Biotage SNAP-Si cartridge (25 g)
  6. washeluting with cyclohexane/ethylacetate from 100-0 to 85/15
  7. customCollected fractions, after solvent evaporation
  8. customafforded the title (D24) (0.5 g)

出典と根拠

ORDレコード
ord-d2e0bd68ea8f4e4da0edbf7e1c4971e9
出典データセット
uspto-grants-2014_09
特許番号
US08828987B2

関連ノート

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