Potassium Carbonate → (3R)-1-[4-(Methanesulfonyl)phenyl]-3-methylpiperazine

HRID 1677752Notes

Reaction equation

HRID 1677752 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8](F)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH3:12][C@@H:13]1[CH2:18][NH:17][CH2:16][CH2:15][NH:14]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:12][C@H:13]1[NH:14][CH2:15][CH2:16][N:17]([C:8]2[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=2)[CH2:18]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 679941-Fluoro-4-(methylsulphonyl)benzeneHCID 73304342-Methylpiperazine, (R)-

Product 1

HCID 26597658(3R)-1-[4-(Methanesulfonyl)phenyl]-3-methylpiperazineYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-fluorophenyl methyl sulfone (2.00 g), (R)-2-methylpiperazine (2.30 g) and K2CO3 (3.20 g) in anhydrous DMF (80 mL) was heated at 100° C. for 5 hours. The reaction mixture was filtered to remove salts and the solvent was evaporated under reduced pressure to give a yellow oil. Purification by flash chromatography (CHCl3/MeOH) gave 1.36 g (47%) of the title compound as a pale yellow solid. M+(ESI): 255.2. HPLC (Condition A), Rt: 1.0 min (HPLC purity: 100%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove salts
  3. customthe solvent was evaporated under reduced pressure
  4. customto give a yellow oil
  5. customPurification by flash chromatography (CHCl3/MeOH)

Sources & evidence

ORD record
ord-f4e2c158cdcd41f990d6be4f0ad00528
Source dataset
uspto-grants-2011_08
Patent number
US08008302B2

Reaction notes

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