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

HRID 2186183Notes

Reaction equation

HRID 2186183 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-4f4b6dca24ba4387865b26743d4f8f13
Source dataset
uspto-grants-2002_06
Patent number
US06403595B1

Reaction notes

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