Dimethylformamide → Ethyl 3-(2-nitrobenzyl)-2-oxo-1-propyl-3-piperidinecarboxylate

HRID 2269721Notes

Reaction equation

HRID 2269721 reaction equation
[H-].[Na+].CN(C=O)C.[N+:8]([C:11]1[CH:29]=[CH:28][CH:27]=[CH:26][C:12]=1[CH2:13][C:14]1([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:19][CH2:18][CH2:17][NH:16][C:15]1=[O:20])([O-:10])=[O:9].[CH2:30](I)[CH2:31][CH3:32]>O>[N+:8]([C:11]1[CH:29]=[CH:28][CH:27]=[CH:26][C:12]=1[CH2:13][C:14]1([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:19][CH2:18][CH2:17][N:16]([CH2:30][CH2:31][CH3:32])[C:15]1=[O:20])([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 18332987HCID 18332987, compound

Product 1

HCID 18332952Ethyl 3-(2-nitrobenzyl)-2-oxo-1-propyl-3-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (60% dispersion in oil, 1.59 g) was added to a DMF solution (100 ml) of ethyl 3-(2-nitrobenzyl)-2-oxo-3-piperidinecarboxylate (11.0 g) and propyl iodide (5.79 ml) under ice-cooling. The reaction mixture was stirred at room temperature for 30 minutes. The reaction mixture was diluted with water and extracted with a mixture of ethyl acetate and diethyl ether. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/4 to 1/2) to obtain the entitled compound (10.6 g).

Workup

  1. temperaturecooling
  2. extractionextracted with a mixture of ethyl acetate and diethyl ether
  3. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/4 to 1/2)

Sources & evidence

ORD record
ord-ed29f519324e4db2987032eac37ae5ec
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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