Methyl iodide → N-[(4-bromophenyl)methyl]-N-methyl-1-pyrrolidinecarboxamide

HRID 230636Notes

Reaction equation

HRID 230636 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:11])=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:20]>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]([CH3:20])[C:10]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57762826N-[(4-bromophenyl)methyl]-1-pyrrolidinecarboxamide

Product 1

HCID 57762825N-[(4-bromophenyl)methyl]-N-methyl-1-pyrrolidinecarboxamideYield 103.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-[(4-bromophenyl)methyl]-1-pyrrolidinecarboxamide (230 mg, 0.81 mmol), was dissolved in dimethylformamide (2 ml) and treated at room temperature with a 60% sodium hydride suspension in mineral oil (33 mg, 0.83 mmol). This mix was stirred for 15 minutes before being treated with iodomethane (116 mg, 0.82 mmol). The resulting mix was stirred at 20° C. for a total of 16.5 hours. The reaction was quenched with water (4 ml) and extracted into ethyl acetate (4 ml). The organic layer was dried over sodium sulphate and the solvent removed under reduced pressure to give the title compound as a colourless oil (250 mg, crude). LC/Mass Spec (ES): Found 297 (ES+), retention time 2.90 mins. C13H1779BrN2O requires 296.

Workup

  1. additionThe resulting mix
  2. stirringwas stirred at 20° C. for a total of 16.5 hours
  3. customThe reaction was quenched with water (4 ml)
  4. extractionextracted into ethyl acetate (4 ml)
  5. dry with materialThe organic layer was dried over sodium sulphate
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-a38f9db399a94e7590119daaa674b8c7
Source dataset
uspto-grants-2009_07
Patent number
US07566735B2

Reaction notes

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