Ethyl Acetate → 4-(3-Bromobenzenesulfonyl)-1-[1-(tert-butoxycarbonyl)-4-piperidylmethyl]-2-piperazinone

HRID 1840595Notes

Reaction equation

HRID 1840595 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]2[CH2:20][CH2:19][NH:18][CH2:17][C:16]2=[O:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C.[Br:34][C:35]1[CH:36]=[C:37]([S:41](Cl)(=[O:43])=[O:42])[CH:38]=[CH:39][CH:40]=1>O>[Br:34][C:35]1[CH:36]=[C:37]([S:41]([N:18]2[CH2:19][CH2:20][N:15]([CH2:14][CH:11]3[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]3)[C:16](=[O:21])[CH2:17]2)(=[O:43])=[O:42])[CH:38]=[CH:39][CH:40]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 17943m-Bromobenzenesulphonyl chlorideHCID 234475144-(2-Oxo-piperazin-1-ylmethyl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 177985604-(3-Bromobenzenesulfonyl)-1-[1-(tert-butoxycarbonyl)-4-piperidylmethyl]-2-piperazinoneYield 50.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 1-[1-(tert-butoxycarbonyl)-4-piperidylmethyl]-2-piperazinone (1.19 g), sodium carbonate (848 mg), ethyl acetate (40 ml) and water (20 ml) was added 3-bromobenzenesulfonyl chloride (1.02 g), and the mixture was stirred at room temperature for 1 hour. The organic layer was separated, washed with saturated brine, dried and concentrated, and the residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:2) to give colorless crystals of the title compound (1.05 g).

Workup

  1. customThe organic layer was separated
  2. washwashed with saturated brine
  3. customdried
  4. concentrationconcentrated
  5. customthe residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-384efd7d97df4dc1a3f2304cafe3d597
Source dataset
uspto-grants-2004_01
Patent number
US06680312B2

Reaction notes

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