Reaction #806274

Reaction equation

4-fluorophenylsulfonyl chloride

triethylamine

1-[bis(4-chlorophenyl)methyl]azetidin-3-ylamine

→

N-{1-[bis(4-chloro-phenyl)methyl]azetidin-3-yl}-4-fluorophenylsulfonamide

Yield 38.7%

Solvents

dichloromethane

Conditions

Workup

1. 1
   Washthe reaction mixture is washed with 10 cm3 of distilled water
2. 2
   Dryingdried over magnesium sulfate
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
5. 5
   OtherThe residue obtained
6. 6
   Otheris purified by flash chromatography on silica gel [eluant: dichloromethane/ethyl acetate (100/0 to 95/5 by volume) gradient]

Procedure

0.214 g of 4-fluorophenylsulfonyl chloride and 0.28 cm3 of triethylamine are added, at room temperature under an argon atmosphere, to a solution of 0.307 g of 1-[bis(4-chlorophenyl)methyl]azetidin-3-ylamine in 10 cm3 of dichloromethane. After stirring for 16 hours at room temperature, the reaction mixture is washed with 10 cm3 of distilled water, dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue obtained is purified by flash chromatography on silica gel [eluant: dichloromethane/ethyl acetate (100/0 to 95/5 by volume) gradient]. 0.18 g of N-{1-[bis(4-chloro-phenyl)methyl]azetidin-3-yl}-4-fluorophenylsulfonamide is obtained in the form of a white foam [1H NMR spectrum (300 MHz, CDCl3, δ in ppm): 2.74 (broad t, J=7.5 Hz: 2H); 2.39 (broad t, J=7.5 Hz: 2H); 3.98 (mt: 1H); 4.20 (s: 1H); 4.79 (d, J=9 Hz: 1H); from 7.10 to 7.35 (mt: 10H); 7.86 (mt: 2H)].

Source