Triethylamine → HCID 10142306, compound

HRID 277133Notes

Reaction equation

HRID 277133 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)[N:16]2[CH2:19][CH:18]([NH:20][CH2:21][C:22]3[CH:27]=[C:26]([F:28])[CH:25]=[C:24]([F:29])[CH:23]=3)[CH2:17]2)=[CH:11][CH:10]=1.[CH3:37][S:38](Cl)(=[O:40])=[O:39]>ClCCl>[Cl:36][C:33]1[CH:34]=[CH:35][C:30]([CH:15]([C:12]2[CH:13]=[CH:14][C:9]([Cl:8])=[CH:10][CH:11]=2)[N:16]2[CH2:17][CH:18]([N:20]([CH2:21][C:22]3[CH:27]=[C:26]([F:28])[CH:25]=[C:24]([F:29])[CH:23]=3)[S:38]([CH3:37])(=[O:40])=[O:39])[CH2:19]2)=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10296513HCID 10296513, compound

Product 1

HCID 10142306HCID 10142306, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

347 mm3 of triethylamine are added, at room temperature under an argon atmosphere, to a solution of 433 mg of N-{1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}-N-(3,5-difluorobenzyl)amine in 30 cm3 of dichloro-methane. The mixture is cooled to around 0° C. before adding thereto a solution of 46.4 mm3 of methylsulfonyl chloride in 5 mm3 of dichloromethane, and then it is stirred at room temperature for 1 hour. The reaction mixture is diluted with 20 cm3 of dichloromethane and is then washed with twice 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 introduced into solution in methanol on a Bond Elut® SCX cartridge (10 g), eluting successively with methanol and with a 1 M solution of ammonia in methanol. The ammoniacal fractions are pooled and concentrated to dryness under reduced pressure (2.7 kPa). 0.44 g of N-{1-[bis(4-chloro-phenyl)methyl]azetidin-3-yl}-N-(3,5-difluorobenzyl)-methylsulfonamide is thus obtained in the form of a cream-colored foam [1H NMR spectrum (300 MHz, CDCl3, δ in ppm): 2.81 (s:3H); 3.02 (broad t, J=7.5 Hz: 2H); 3.38 (broad t, J=7.5 Hz:2H); 4.23 (s:1H); 4.40 (mt:1H); 4.54 (s:2H); 6.75 (tt, J=9 and 2 Hz:1H); 6.95 (mt:2H); 7.25 (mt:8H)].

Workup

  1. additionbefore adding
  2. washis then washed with twice 20 cm3 of distilled water
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  6. additionThe residue is introduced into solution in methanol on a Bond Elut® SCX cartridge (10 g)
  7. washeluting successively with methanol and with a 1 M solution of ammonia in methanol
  8. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-d67aeea502a242e68d987cc6dda1a1f1
Source dataset
uspto-grants-2002_03
Patent number
US06355631B1

Reaction notes

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