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

HRID 603240Notes

Reaction equation

HRID 603240 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-1105be3e82d14c6e999d01a513fb6487
Source dataset
uspto-grants-2011_03
Patent number
US07906645B2

Reaction notes

Loading…