Ethyl Bromide → N-(3,4-Dichlorophenyl)-4-[(1-ethylpiperidin-3-yl)carbonyl]piperazine-1-carboxamide

HRID 2371196Notes

Reaction equation

HRID 2371196 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([NH:10][C:11]([N:13]2[CH2:18][CH2:17][N:16]([C:19]([CH:21]3[CH2:26][CH2:25][CH2:24][NH:23][CH2:22]3)=[O:20])[CH2:15][CH2:14]2)=[O:12])[CH:6]=[CH:7][C:8]=1[Cl:9].C(=O)([O-])[O-].[K+].[K+].[CH2:33](Br)[CH3:34]>CN(C)C=O>[Cl:2][C:3]1[CH:4]=[C:5]([NH:10][C:11]([N:13]2[CH2:14][CH2:15][N:16]([C:19]([CH:21]3[CH2:26][CH2:25][CH2:24][N:23]([CH2:33][CH3:34])[CH2:22]3)=[O:20])[CH2:17][CH2:18]2)=[O:12])[CH:6]=[CH:7][C:8]=1[Cl:9]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 67220795N-(3,4-dichlorophenyl)-4-(piperidin-3-ylcarbonyl)piperazine-1-carboxamide hydrochloride

Product 1

HCID 11582353N-(3,4-Dichlorophenyl)-4-[(1-ethylpiperidin-3-yl)carbonyl]piperazine-1-carboxamideYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(3,4-dichlorophenyl)-4-(piperidin-3-ylcarbonyl)piperazine-1-carboxamide hydrochloride (200 mg) in dimethylformamide (10 mL) was added potassium carbonate (138 mg) and ethyl bromide (0.035 mL). The reaction mixture was stirred overnight. The reaction mixture was partitioned between dichloromethane and water and the organic layer was washed with brine. The organic extract was dried over sodium sulfate and evaporated. The residue was purified by silica column chromatography, eluting with a gradient of 0 to 10% MeOH in dichloromethane to give the title compound as a white solid (94 mg, 48%).

Workup

  1. customThe reaction mixture was partitioned between dichloromethane and water
  2. washthe organic layer was washed with brine
  3. extractionThe organic extract
  4. dry with materialwas dried over sodium sulfate
  5. customevaporated
  6. customThe residue was purified by silica column chromatography
  7. washeluting with a gradient of 0 to 10% MeOH in dichloromethane

Sources & evidence

ORD record
ord-f7ede2bb341a41c5967a1150cbfd46fe
Source dataset
uspto-grants-2014_04
Patent number
US08710224B2

Reaction notes

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