Methyl iodide → HCID 71138513, compound

HRID 1852919Notes

Reaction equation

HRID 1852919 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:17])[CH3:16])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].I[CH3:21]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:9][CH2:10][CH:11]([N:14]([CH3:21])[C:15](=[O:17])[CH3:16])[CH2:12][CH2:13]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 71138602HCID 71138602, compound

Product 1

HCID 71138513HCID 71138513, compoundYield 103.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-[1-(3-bromophenyl)-4-piperidyl]acetamide (11.6 g, 39.2 mmol) in THF (392 mL) was added to sodium hydride (6.84 g, 55% in mineral oil, 157 mmol) portionwise at 0° C. and stirred at room temperature for 10 minutes under nitrogen. The reaction mixture was added to iodomethane (7.32 mL, 118 mmol) at 0° C. and stirred at room temperature for 6 hours. The mixture was slowly quenched with water at 0° C. and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and filtered through a Celite pad. The combined filtrate and washings were concentrated. The residue was purified by silica gel column chromatography (hexane/AcOEt=80:20→0:100) to afford desired product (12.6 g, quant.) as brown oil.

Workup

  1. stirringstirred at room temperature for 6 hours
  2. customThe mixture was slowly quenched with water at 0° C.
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered through a Celite pad
  7. concentrationThe combined filtrate and washings were concentrated
  8. customThe residue was purified by silica gel column chromatography (hexane/AcOEt=80:20→0:100)

Sources & evidence

ORD record
ord-781fbac315e44eb6a239462d20791065
Source dataset
uspto-grants-2015_02
Patent number
US08962619B2

Reaction notes

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