Methyl iodide → Ethyl 1-benzyl-3-methyl-4-oxopiperidine-3-carboxylate

HRID 1063342Notes

Reaction equation

HRID 1063342 reaction equation
Cl.[CH2:2]([O:4][C:5]([CH:7]1[C:12](=[O:13])[CH2:11][CH2:10][N:9]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:8]1)=[O:6])[CH3:3].[CH2:21]1COCC1.[OH-].[K+].CI>CN(C=O)C>[CH2:2]([O:4][C:5]([C:7]1([CH3:21])[C:12](=[O:13])[CH2:11][CH2:10][N:9]([CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:8]1)=[O:6])[CH3:3]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 102623Ethyl 1-benzyl-4-oxopiperidine-3-carboxylate hydrochloride

Product 1

HCID 14666544Ethyl 1-benzyl-3-methyl-4-oxopiperidine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl-1-benzyl-4-oxo-piperidine-3-carboxylate hydrochloride (150 g, 0.504 mol) was suspended in a solvent mixture of 750 ml THF and 750 ml DMF at room temperature. Addition of powdered KOH (56 g, 1.0 mol) was made in two equal lots keeping half an hour interval between two additions. To a clear reaction mixture methyl iodide (78 g, 0.55 mol) was added over period of 10 minutes and it was stirred for three hours at room temperature. The reaction was quenched by adding 4 ltr water followed by 1.5 ltr diethyl ether. Layers were separated. Organic layer was washed with water and dried over Na2SO4. Evaporation of organic solvent afforded a liquid, which was passed through a silica gel column to give 86 g (61%), titled compound.

Workup

  1. waitkeeping half an hour
  2. customThe reaction was quenched
  3. additionby adding 4 ltr water
  4. customLayers were separated
  5. washOrganic layer was washed with water
  6. dry with materialdried over Na2SO4
  7. customEvaporation of organic solvent
  8. customafforded a liquid, which

Sources & evidence

ORD record
ord-f4f317f106674be0a0cf1e52c48ca580
Source dataset
uspto-grants-2005_11
Patent number
US06964966B2

Reaction notes

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