Dimethylamine, hydrochloride → HCID 61228595, compound

HRID 1054889Notes

Reaction equation

HRID 1054889 reaction equation
Cl.[CH3:2][NH:3][CH3:4].[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8](F)[N:7]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:5][C:6]1[N:7]=[C:8]([N:3]([CH3:4])[CH3:2])[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 739342,6-Difluoropyridine

Product 1

HCID 61228595HCID 61228595, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Dimethylamine hydrochloride (19.0 g, 91.2 mmol) was added to a suspension of 2,6-difluoropyridine (10.0 g, 86.9 mmol) and potassium carbonate (24.4 g, 177 mmol) in acetonitrile (100 mL). The suspension was stirred at reflux for 2 h before cooling to room temperature and filtering through a pad of celite, washing the filter cake with acetonitrile (500 mL). The filtrate was concentrated in vacuo to product desired product (11.3 g, 93% yield) as an orange oil. 1H NMR (CDCl3, 600 MHz) 5=7.33-7.66 (m, 1 H) 6.28 (dd, J=8.22, 2.35 Hz, 1 H) 6.09 (dd, J=7.63, 2.35 Hz, 1 H) 3.07 (s, 6 H); MS (FID)=140.0 (M)+.

Workup

  1. temperatureat reflux for 2 h
  2. filtrationfiltering through a pad of celite
  3. washwashing the filter cake with acetonitrile (500 mL)

Sources & evidence

ORD record
ord-fbfb1d5e7977401c99aef513f17c4e64
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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