Methyl iodide → 1-tert-Butoxycarbonyl-4-{4-[methyl(methylsulfonyl)amino]benzyl}piperidine

HRID 1394335Notes

Reaction equation

HRID 1394335 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:28]I>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]([CH3:28])[S:22]([CH3:25])(=[O:24])=[O:23])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18538690HCID 18538690, compound

Product 1

HCID 185389231-tert-Butoxycarbonyl-4-{4-[methyl(methylsulfonyl)amino]benzyl}piperidineYield 82.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-tert-Butoxycarbonyl-4-[4-(methylsulfonyl)aminobenzyl]piperidine (1.4 g, 3.81 mmol) was dissolved in N,N-dimethylformamide (10 mL). To the solution was added 72% sodium hydride in mineral oil (143 mg, 4.29 mmol) under ice cooling, and the mixture was stirred for 10 minutes. To the mixture was added methyl iodide (0.25 mL, 4 mmol), and the mixture was stirred at room temperature for 1 hour. After cooling, the reaction mixture was poured into ice-water (20 mL) and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the concentrate was purified by silica gel column chromatography (hexane/ethyl acetate=3/2) to give the titled compound (1.20 g) as colorless powdery crystals.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water and saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe concentrate was purified by silica gel column chromatography (hexane/ethyl acetate=3/2)

Sources & evidence

ORD record
ord-5e5f50480dbe4fd7a408ffa2eeb28078
Source dataset
uspto-grants-2008_03
Patent number
US07348324B2

Reaction notes

Loading…