Potassium Acetate → 1-[1-(Tert-butoxycarbonyl)-4-piperidylmethyl]-4-[4-(hydroxymethyl)benzenesulfonyl]-2-piperazinone

HRID 1840596Notes

Reaction equation

HRID 1840596 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]3)[C:14](=[O:32])[CH2:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.C([O-])(=[O:35])C.[K+]>CN(C=O)C>[C:28]([O:27][C:25]([N:22]1[CH2:23][CH2:24][CH:19]([CH2:18][N:15]2[CH2:16][CH2:17][N:12]([S:9]([C:6]3[CH:5]=[CH:4][C:3]([CH2:2][OH:35])=[CH:8][CH:7]=3)(=[O:11])=[O:10])[CH2:13][C:14]2=[O:32])[CH2:20][CH2:21]1)=[O:26])([CH3:30])([CH3:29])[CH3:31]

Participants

4

Reactant 2

HCID 517044Potassium AcetateHCID 234476104-[4-(Bromomethyl)benzenesulfonyl]-1-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]-2-piperazinone

Product 1

HCID 177986031-[1-(Tert-butoxycarbonyl)-4-piperidylmethyl]-4-[4-(hydroxymethyl)benzenesulfonyl]-2-piperazinoneYield 80.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-[4-(bromomethyl)benzenesulfonyl]-1-[1-(tert-butoxycarbonyl)-4-piperidylmethyl]-2-piperazinone (2.85 g) in DMF (30 ml) was added potassium acetate (1.58 g), and the mixture was stirred at 60° C. for 4 hours. The reaction solution was concentrated under reduced pressure, and to the residue was added ethyl acetate. The mixture was washed with water and saturated brine, dried and concentrated, and the residue was dissolved in methanol (50 ml). To the solution was added sodium methoxide (28% methanol solution, 290 mg), and the mixture was stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure, and to the residue was added ethyl acetate. The mixture was washed with water and saturated brine, dried (MgSO4) and concentrated. The residual crystals were washed with ether to give colorless crystals of 1-[1-(tert-butoxycarbonyl)-4-piperidylmethyl]-4-[4-(hydroxymethyl)benzenesulfonyl]-2-piperazinone (2.02 g).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionto the residue was added ethyl acetate
  3. washThe mixture was washed with water and saturated brine
  4. customdried
  5. concentrationconcentrated
  6. dissolutionthe residue was dissolved in methanol (50 ml)
  7. additionTo the solution was added sodium methoxide (28% methanol solution, 290 mg)
  8. stirringthe mixture was stirred at room temperature for 2 hours
  9. concentrationThe reaction solution was concentrated under reduced pressure
  10. additionto the residue was added ethyl acetate
  11. washThe mixture was washed with water and saturated brine
  12. dry with materialdried (MgSO4)
  13. concentrationconcentrated
  14. washThe residual crystals were washed with ether

Sources & evidence

ORD record
ord-0e3a18beff3e40978bb3ef84a50ead50
Source dataset
uspto-grants-2004_01
Patent number
US06680312B2

Reaction notes

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