HCID 178418361, compound → HCID 178527242, compound

HRID 277137Notes

Reaction equation

HRID 277137 reaction equation
C([N:14]1[CH2:17][CH:16]([N:18]([CH2:22][C:23]2[CH:28]=[C:27]([F:29])[CH:26]=[C:25]([F:30])[CH:24]=2)[SH:19](=[O:21])=[O:20])[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.[H][H]>Cl.C(O)(=O)C.[OH-].[Pd+2].[OH-]>[NH:14]1[CH2:17][CH:16]([N:18]([CH2:22][C:23]2[CH:28]=[C:27]([F:29])[CH:26]=[C:25]([F:30])[CH:24]=2)[SH:19](=[O:20])=[O:21])[CH2:15]1

Participants

6

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178527243HCID 178527243, compound

Product 1

HCID 178527242HCID 178527242, compoundYield 102.9%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

N-Azetidin-3-yl-N-(3,5-difluorophenyl)methylsulfonamide hydrochloride is obtained in the following manner: in a 500-cm3 hydrogenator, a solution of 1 g of N-(1-benzhydrylazetidin-3-yl)-N-(3,5-difluorophenyl)methylsulfonamide in a mixture of 2.5 cm3 of 1M hydrochloric acid and 0.41 cm3 of acetic acid is hydrogenated in the presence of 0.161 g of palladium hydroxide at a hydrogen pressure of 30 bar for 4 hours. The catalyst is removed by filtration on a celite bed and then the filtrate is concentrated to dryness at 40° C. under 2.7 kPa to give 630 mg of N-azetidin-3-yl-N-(3,5-difluorophenyl)methylsulfonamide, melting at 216° C.

Workup

  1. customThe catalyst is removed by filtration on a celite bed
  2. concentrationthe filtrate is concentrated to dryness at 40° C. under 2.7 kPa

Sources & evidence

ORD record
ord-9a13a606fcdf45f3826491d3aac7394f
Source dataset
uspto-grants-2002_03
Patent number
US06355631B1

Reaction notes

Loading…