Methyl iodide → HCID 70873347, compound

HRID 2172245Notes

Reaction equation

HRID 2172245 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][C:20]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=3)([OH:23])[CH2:19][CH2:18]2)=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.I[CH3:35]>CN(C)C=O>[CH2:3]([O:10][C:11]1[CH:12]=[CH:13][C:14]([N:17]2[CH2:18][CH2:19][C:20]([O:23][CH3:35])([C:24]3[CH:25]=[CH:26][C:27]([C:30]([F:33])([F:31])[F:32])=[CH:28][CH:29]=3)[CH2:21][CH2:22]2)=[CH:15][CH:16]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 70873515HCID 70873515, compound

Product 1

HCID 70873347HCID 70873347, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

60% sodium hydride (0.225 g, 5.2 mmol) was added to an N,N-dimethylformamide solution (20 ml) of 1-(4-benzyloxyphenyl)-4-(4-trifluoromethylphenyl)piperidin-4-ol (2 g, 4.7 mmol) and iodomethane (0.585 ml, 9.4 mmol) under an argon atmosphere while ice cooling, followed by stirring at the same temperature. After 2 hours, the mixture was poured into ice water, and the precipitate was collected by filtration. The resulting solid was dissolved in ethyl acetate/dichloromethane and dried over sodium sulfate. After removing the desiccant by filtration, the solvent was distilled off. The residue was purified by silica gel column chromatography (dichloromethane:ethyl acetate=100:0→95:5) to afford the title compound as a white powder (1.64 g, 79%).

Workup

  1. filtrationthe precipitate was collected by filtration
  2. dissolutionThe resulting solid was dissolved in ethyl acetate/dichloromethane
  3. dry with materialdried over sodium sulfate
  4. customAfter removing the
  5. filtrationdesiccant by filtration
  6. distillationthe solvent was distilled off
  7. customThe residue was purified by silica gel column chromatography (dichloromethane:ethyl acetate=100:0→95:5)

Sources & evidence

ORD record
ord-7e335a9bb1ae4040804c5628b7ec391d
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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