Potassium Carbonate → HCID 86596310, compound

HRID 1392914Notes

Reaction equation

HRID 1392914 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][N:3]=1.[CH3:10][NH:11][CH2:12][CH3:13].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][CH:12]([NH:11][CH3:10])[CH3:13])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12219N-MethylethylamineHCID 1554792-Chloro-5-(chloromethyl)pyridine

Product 1

HCID 86596310HCID 86596310, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-chloro-5-(chloromethyl)pyridine (1.0 g, 6.17 mmole) in 11 mL of dry acetonitrile is added 1.06 mL (12.3 mmol) of methylethylamine followed by 850 mg (6.17 mmol) of potassium carbonate. The reaction is heated at 80° C. for 5 h. After cooling, the reaction mixture is quenched with 5 mL of water, extracted three-times with methylene chloride, and dried over sodium sulfate. Concentration of the solvent provided an oil which was purified by silica gel chromatography to provide 1.0 g (87% yield) of 1-(6-Chloro-pyridin-3-ylmethyl)-methylethylamine. Diagnostic 1H NMR (400 MHz, CDCl3) 1.06 (t, 3H, J=7.1 Hz), 2.14 (s, 3H), 2.40 (q, 2H, J=7.1 Hz), 3.43 (s, 2H), 7.25 (d, 1H, J=8.2 Hz), 7.62 (dd, 1H, J=8.2 and 5.8 Hz); MS (187.2 (M+H).

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture is quenched with 5 mL of water
  3. extractionextracted three-times with methylene chloride
  4. dry with materialdried over sodium sulfate
  5. customConcentration of the solvent provided an oil which
  6. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-09c2fbf6e56d4daa88040db09c493fac
Source dataset
uspto-grants-2008_03
Patent number
US07345038B2

Reaction notes

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