Methyl iodide → Diisopropyl Ether

HRID 49795Notes

Reaction equation

HRID 49795 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([NH:10][C:11](=[O:19])[C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[H-].[Na+].[CH3:22]I.[C:24]([O:27][CH2:28][CH3:29])(=O)C>CN(C)C=O.O>[CH:28]([O:27][CH:17]([CH3:16])[CH3:12])([CH3:29])[CH3:22].[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([N:10]([CH3:24])[C:11](=[O:19])[C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 9816738Benzamide, N-(1-acetyl-4-piperidinyl)-4-fluoro-

Product 2

HCID 7914Diisopropyl EtherHCID 9817095N-(1-acetylpiperidin-4-yl)-N-methyl-4-fluorobenzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(1-acetylpiperidin-4-yl)-4-fluorobenzamide (529 mg) in N,N-dimethylformamide (5 ml) was added sodium hydride (0.1 g). After stirring for 45 minutes, methyl iodide (623 ml) was added to the solution. After stirring for 45 minutes, the mixture was diluted with ethyl acetate (100 ml) and water (50 ml). An organic phase was separated, and washed with water and brine. After drying with magnesium sulfate, the solvents were removed under reduced pressure. After trituration with diisopropyl ether, N-(1-acetylpiperidin-4-yl)-N-methyl-4-fluorobenzamide (248 mg) was obtained.

Workup

  1. stirringAfter stirring for 45 minutes
  2. customAn organic phase was separated
  3. washwashed with water and brine
  4. dry with materialAfter drying with magnesium sulfate
  5. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-dfc6e9725237477faeba07e011dfd021
Source dataset
uspto-grants-2004_03
Patent number
US06710043B1

Reaction notes

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