Potassium Carbonate → HCID 61034625, compound

HRID 1392905Notes

Reaction equation

HRID 1392905 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][N:3]=1.C[CH:11]([NH2:15])[CH2:12][O:13][CH3:14].[C:16](=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][N:15]([CH2:11][CH2:12][O:13][CH3:14])[CH3:16])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123458MethoxyisopropylamineHCID 1554792-Chloro-5-(chloromethyl)pyridine

Product 1

HCID 61034625HCID 61034625, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-chloro-5-(chloromethyl)pyridine (384 mg, 2.37 mmole) in 4 mL of dry acetonitrile is 0.51 mL (4.74 mmol) of 1-methyl-2-methoxyethylamine followed by 328 mg (2.37 mmol) of potassium carbonate. The reaction is heated at 80° C. for 3 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 395 mg (78% yield) of (6-Chloro-pyridin-3-ylmethyl)-(2-methoxy-ethyl)-methyl-amine. Diagnostic 1H NMR (400 MHz, CDCl3) 2.25 (s, 3H), 2.59 (t, 2H, J=5.6 Hz), 3.32 (s, 3H), 3.49 (t, 2H, J=5.6 hz), 7.26 (d, 1H, J=8.5 Hz), 7.68 (dd, 1H, J=8.3 and 2.5 Hz), 8.27 9d, 1H, J=1.6 Hz); MS 215.2 (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-03667cd958e44183b2d2915751881928
Source dataset
uspto-grants-2008_03
Patent number
US07345038B2

Reaction notes

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