Potassium Carbonate → HCID 82674546, compound

HRID 1392915Notes

Reaction equation

HRID 1392915 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][N:3]=1.[NH2:10][CH:11]([CH3:15])[CH2:12][O:13][CH3:14].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][NH:10][CH:11]([CH3:15])[CH2:12][O:13][CH3:14])=[CH:6][CH:7]=1

Participants

5

Reactant 3

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

Product 1

HCID 82674546HCID 82674546, compoundYield 48.3%

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 1.30 mL (12.3 mmol) of 2-amino-1-methoxypropane 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 640 mg (48% yield) of (6-Chloro-pyridin-3-ylmethyl)-(2-methoxy-1-methyl-ethyl)-amine. Diagnostic C13 NMR (100 MHz, CDCl3) 17.2, 48.0, 52.3, 59.1, 77.2, 124.1, 135.3, 138.9, 149.5, 150.1 MS (217.2 (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-5360a3b437ef4e2e95b6f991a6407445
Source dataset
uspto-grants-2008_03
Patent number
US07345038B2

Reaction notes

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