Reaction #806276

Reaction equation

ethyl acetate

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

sodium hydride

iodomethane

→

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

Solvents

tetrahydrofuran

tetrahydrofuran

water

Conditions

Workup

1. 1
   workup.STIRRINGafter stirring for an additional 16 hours
2. 2
   DryingThe organic phase is dried over magnesium sulfate
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
5. 5
   OtherThe residue is purified by flash chromatography on silica gel [eluant: cyclohexane/ethyl acetate (90/10 by volume)]

Procedure

A solution of 0.26 g of N-{1-[bis(4-chloro-phenyl)methyl]azetidin-3-yl}-4-fluorophenylsulfonamide in 5 cm3 of tetrahydrofuran is added, at room temperature under an argon atmosphere, to a suspension of 20.5 mg of 80% sodium hydride in 10 cm3 of tetrahydrofuran. After stirring for 1 hour at around 20° C., 60 mm3 of iodomethane are added and then after stirring for an additional 16 hours, the suspension is supplemented with 30 cm3 of ethyl acetate and 20 cm3 of distilled water. The organic phase is dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue is purified by flash chromatography on silica gel [eluant: cyclohexane/ethyl acetate (90/10 by volume)]. 19 mg of N-{1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}-N-methyl-4-fluorophenylsulfonamide are thus obtained in the form of a white powder [1H NMR spectrum (300 MHz, CDCl3, δ in ppm): 2.69 (s: 3H); 3.02 (split t, J=7 and 2 Hz: 2H); 3.35 (split t, J=7 and 2 Hz: 2H); 3.91 (mt: 1H); 4.27 (s: 1H); from 7.15 to 7.35 (mt: 10H); 7.75 (dd, J=9 and 5 Hz: 2H)].

Source