Potassium Carbonate → N-methyl-tert-Butyl-(6-chloro-pyridin-3-ylmethyl)-amine

HRID 1392910Notes

Reaction equation

HRID 1392910 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][C:12]([CH3:15])([CH3:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:10][N:11]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:8][C:5]1[CH:4]=[N:3][C:2]([Cl:1])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 84552N-Methyl-tert-butylamineHCID 1554792-Chloro-5-(chloromethyl)pyridine

Product 1

HCID 85999423N-methyl-tert-Butyl-(6-chloro-pyridin-3-ylmethyl)-amineYield 56.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-chloro-5-(chloromethyl)pyridine (570 mg, 3.52 mmole) in 7 mL of dry acetonitrile is 608 mg (7.04 mmol) of N-methyl-t-butylamine followed by 486 mg (3.52 mmol) of potassium carbonate. The reaction is heated at 80° C. for 12 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 420 mg (56% yield) of N-methyl-tert-Butyl-(6-chloro-pyridin-3-ylmethyl)-amine. Diagnostic 1H NMR (400 MHz, CDCl3) 1.14 (s, 9H), 2.06 (s, 3H), 3.48 (s, 2H), 7.26 (d, 1H, J=6.2 Hz), 7.68 (d, 1 h, J=6.6 Hz), 8.28 (d, 1H, J=2.5 Hz); MS 213.3 (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-ecfc8237a80946d29cb09af9a5f643e9
Source dataset
uspto-grants-2008_03
Patent number
US07345038B2

Reaction notes

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