Methyl iodide → trans-3-Ethoxycarbonyl-4-(4'-fluorophenyl)-1-methylpiperidine-2,6-dione

HRID 1199801Notes

Reaction equation

HRID 1199801 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[C@H:11]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:10][C:9](=[O:19])[NH:8][C:7]1=[O:20])=[O:5])[CH3:2].CI.[C:23](=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH2:1]([O:3][C:4]([C@H:6]1[C@H:11]([C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)[CH2:10][C:9](=[O:19])[N:8]([CH3:23])[C:7]1=[O:20])=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 11391819(+/-)-trans-3-Ethoxycarbonyl-4(4'-fluorophenyl)piperidin-2,6-dione2×

Product 1

HCID 15405466trans-3-Ethoxycarbonyl-4-(4'-fluorophenyl)-1-methylpiperidine-2,6-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of compound E1 (±)-trans-3-ethoxycarbonyl-4(4'-fluorophenyl)piperidin-2,6-dione (1.0 g) in anhydrous dimethylformamide was stirred and cooled to about 0° and methyl iodide (0.67 g) and anhydrous potassium carbonate (0.51 g) added. The mixture was stirred at 0°-2° for 7.5 hours, after which it was diluted with water and extracted with ethyl acetate (100 ml). The extract was washed with water, brine and dried over anhydrous sodium sulphate. Evaporation gave the title compound as a pale yellow oil, ca. 90% pure by n.m.r. spectroscopy.

Workup

  1. temperaturecooled to about 0°
  2. extractionextracted with ethyl acetate (100 ml)
  3. washThe extract was washed with water, brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. customEvaporation

Sources & evidence

ORD record
ord-7465470b030a4a4aa9f618715b231ddb
Source dataset
uspto-grants-1990_02
Patent number
US04902801

Reaction notes

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