Reaction #806275

Reaction equation

pyrrolidine

N-{1-[bis(4-chlorophenyl)-methyl]azetidin-3-yl}-(3,5-difluorophenyl)sulfonamide

→

N-{1-[bis(4-chlorophenyl)-methyl]azetidin-3-yl}-(3-fluoro-5-pyrrolidin-1-ylphenyl)sulfonamide

Solvents

dichloromethane

dimethyl sulfoxide

Conditions

Workup

1. 1
   Washwashed with three times 30 cm3 of distilled water
2. 2
   DryingThe organic phased 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
6. 6
   Washeluting with dichloromethane

Procedure

0.104 cm3 of pyrrolidine is added, at room temperature, to 0.24 g of N-{1-[bis(4-chlorophenyl)-methyl]azetidin-3-yl}-(3,5-difluorophenyl)sulfonamide in solution in 6 cm3 of dimethyl sulfoxide and then the mixture is heated for 18 hours at 90° C. The reaction mixture is diluted with 30 cm3 of dichloromethane and washed with three times 30 cm3 of distilled water. The organic phased 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, eluting with dichloromethane. 50 mg of N-{1-[bis(4-chlorophenyl)-methyl]azetidin-3-yl}-(3-fluoro-5-pyrrolidin-1-ylphenyl)sulfonamide are thus obtained in the form of a white powder [1H NMR spectrum (600 MHz, CDCl3 with addition of a few drops of CD3COOD d4, δ in ppm): 2.04 (mt: 4H); from 3.20 to 3.35 (mt: 6H); 3.60 (t, J=8.5 Hz: 2H); 4.14 (mt: 1H); 4.57 (s: 1H); 6.31 (broad d, J=11.5 Hz: 1H); 6.70 (broad d, J=8.5 Hz: 1H); 6.72 (broad s: 1H); from 7.20 to 7.35 (mt: 8H)].

Source