2-Fluorobenzenesulphonyl chloride → 2-(2-Fluoro-benzenesulfonyl)-octahydro-pyrido[1,2-a]pyrazin-6-one

HRID 2194362Notes

Reaction equation

HRID 2194362 reaction equation
[CH2:1]1[NH:6][CH2:5][CH2:4][N:3]2[C:7](=[O:11])[CH2:8][CH2:9][CH2:10][CH:2]12.[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[S:19](Cl)(=[O:21])=[O:20]>C(Cl)Cl.CC#N>[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[S:19]([N:6]1[CH2:5][CH2:4][N:3]2[C:7](=[O:11])[CH2:8][CH2:9][CH2:10][CH:2]2[CH2:1]1)(=[O:21])=[O:20]

Participants

5

Reactant 2

HCID 1377612-Fluorobenzenesulphonyl chlorideHCID 22562193Hexahydro-1H-pyrido[1,2-a]pyrazin-6(2H)-one

Product 1

HCID 441929292-(2-Fluoro-benzenesulfonyl)-octahydro-pyrido[1,2-a]pyrazin-6-oneYield 44.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of octahydro-pyrido[1,2-a]pyrazin-6-one (compound of Description 12, 20 mg, 0.13 mmol) in DCM (1 ml), TEA (16 mg, 0.16 mmol) and a solution of 2-fluoro-benzenesulfonyl chloride (25 mg, 0.13 mmol) in CH3CN (1 ml) were added at 0° C. After stirring 3 hours at room temperature, the solvent was evaporated. The residue was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried (Na2SO4) and evaporated under reduced pressure. The residue was purified by flash chromatography (from DCM to DCM/MeOH/32% NH4OH 95/5/0.5 respectively) to afford the title compound (18 mg, 44% yield).

Workup

  1. customthe solvent was evaporated
  2. customThe residue was partitioned between water and ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated under reduced pressure
  6. customThe residue was purified by flash chromatography (from DCM to DCM/MeOH/32% NH4OH 95/5/0.5 respectively)

Sources & evidence

ORD record
ord-139eec7709f44ef88444b5518247a3d6
Source dataset
uspto-grants-2012_12
Patent number
US08334286B2

Reaction notes

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