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Ethyl Bromide → N-(3,4-Dichlorophenyl)-1-{[(3R)-1-ethylpiperidin-3-yl]methyl}piperidine-4-carboxamide

HRID 2371191
Notes
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Reaction equation

HRID 2371191 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([CH:12]2[CH2:17][CH2:16][N:15]([CH2:18][C@@H:19]3[CH2:24][CH2:23][CH2:22][NH:21][CH2:20]3)[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].C(=O)([O-])[O-].[K+].[K+].[CH2:31](Br)[CH3:32]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([CH:12]2[CH2:13][CH2:14][N:15]([CH2:18][C@@H:19]3[CH2:24][CH2:23][CH2:22][N:21]([CH2:31][CH3:32])[CH2:20]3)[CH2:16][CH2:17]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 57656947N-(3,4-dichlorophenyl)-1-[(3R)-piperidin-3-ylmethyl]piperidine-4-carboxamide

Product 1

HCID 11632679N-(3,4-Dichlorophenyl)-1-{[(3R)-1-ethylpiperidin-3-yl]methyl}piperidine-4-carboxamideYield 74%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

A mixture of N-(3,4-dichlorophenyl)-1-[(3R)-piperidin-3-ylmethyl]piperidine-4-carboxamide (100 mg), potassium carbonate (41 mg) and ethyl bromide (0.022 mL) in dimethylformamide (4 ml) was stirred at room temperature for 24 hours. The reaction mixture was partitioned between dichloromethane and water. The organic layer was separated, dried over magnesium sulfate and evaporated. The residue was purified by silica column chromatography, eluting with a gradient of 0 to 10% 7M NH3/MeOH in dichloromethane to give the title compound as a white solid (80 mg, 74%).

Workup

  1. customThe reaction mixture was partitioned between dichloromethane and water
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by silica column chromatography
  6. washeluting with a gradient of 0 to 10% 7M NH3/MeOH in dichloromethane

Sources & evidence

ORD record
ord-a3a803a19eb94fc1a1bc9626945ad59d
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08710224B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes