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

HRID 72402

Reaction equation

HRID 72402 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

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

Conditions

Temperature
100 °C

Procedure

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)

Workup

  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)

Sources & evidence

ORD record
ord-d2e0bd68ea8f4e4da0edbf7e1c4971e9
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Linked notes

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