Dimethylformamide → HCID 71268660, compound

HRID 70785Notes

Reaction equation

HRID 70785 reaction equation
[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].CN(C=O)C.Cl.[CH3:21][C:22]1([C:28]([NH2:30])=[O:29])[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>CCOC(C)=O.O>[CH2:1]([N:25]1[CH2:26][CH2:27][C:22]([CH3:21])([C:28]([NH2:30])=[O:29])[CH2:23][CH2:24]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7503Benzyl ChlorideHCID 10340Sodium CarbonateHCID 675063694-Methyl-piperidine-4-carboxylic acid aMide hydrochloride

Product 1

HCID 71268660HCID 71268660, compoundYield 97.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Benzyl chloride (1.90 g) and sodium carbonate (1.59 g) were added to a DMF (70 ml) suspension of 4-methylpiperidine-4-carboxamide hydrochloride (2.24 g), and stirring was performed at room temperature for 16 hours. After adding water to the reaction liquid, extraction was performed with EtOAc. The organic layer was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (MeOH/chloroform) to obtain 1-benzyl-4-methylpiperidine-4-carboxamide (2.85 g).

Workup

  1. customto the reaction liquid, extraction
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (MeOH/chloroform)

Sources & evidence

ORD record
ord-7dc46dc1d2794a90b2f0c8c24f019f0b
Source dataset
uspto-grants-2014_09
Patent number
US08822688B2

Reaction notes

Loading…