Benzyl Bromide → 4-[[4-Methoxybenzenesulfonyl](benzyl)amino]-1-[benzyl]-4-[carbomethoxy]-piperidine

HRID 264308Notes

Reaction equation

HRID 264308 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:13]2([C:19]([O:21][CH3:22])=[O:20])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[H-].[Na+].[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([N:12]([CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:13]2([C:19]([O:21][CH3:22])=[O:20])[CH2:14][CH2:15][N:16]([CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:17][CH2:18]2)(=[O:11])=[O:10])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 229070894-[[4-Methoxybenzenesulfonyl](benzyl)amino]-4-[carbomethoxy]piperidine

Product 1

HCID 229070954-[[4-Methoxybenzenesulfonyl](benzyl)amino]-1-[benzyl]-4-[carbomethoxy]-piperidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[[4-methoxybenzenesulfonyl](benzyl)amino]-4-[carbomethoxy]-piperidine (1.0 g, 2.39 mmol) in dimethylformamide (160 mL) is added sodium hydride (287.0 mg, 7.18 mmol, 60% in oil) at 0° C., followed by benzyl bromide (450.0 mg, 2.63 mmol). The reaction mixture is slowly warmed to room temperature and stirred overnight. The mixture is quenched with water and extracted with ethyl acetate. The combined organic layers are washed with brine, dried (Na2SO4) and the solvent is evaporated to give 4-[[4-methoxybenzenesulfonyl](benzyl)amino]-1- [benzyl]-4-[carbomethoxy]-piperidine.

Workup

  1. customThe mixture is quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried (Na2SO4)
  5. customthe solvent is evaporated

Sources & evidence

ORD record
ord-1ffb476c79a64d2ba707332e8cfe9f75
Source dataset
uspto-grants-1997_07
Patent number
US05646167

Reaction notes

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