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

HRID 72402

반응식

HRID 72402 반응식
[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

참가 물질

4

반응물 3

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

생성물 1

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

반응 조건

온도
100 °C

실험 절차

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)

후처리

  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)

출처 및 근거

ORD 기록
ord-d2e0bd68ea8f4e4da0edbf7e1c4971e9
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08828987B2

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