Potassium Carbonate → HCID 43267162, compound

HRID 1392906Notes

Reaction equation

HRID 1392906 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][CH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][N:11]([CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH3:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 7020624N-methylcyclopentanamine

Product 1

HCID 43267162HCID 43267162, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-chloro-5-(chloromethyl)pyridine (318 mg, 1.96 mmole) in 4 mL of dry acetonitrile is 395 mg (3.92 mmol) of N-methylcyclopentylamine followed by 270 mg (1.96 mmol) of potassium carbonate. The reaction is heated at 80° C. for 20 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 340 mg (77% yield) of (6-Chloro-pyridin-3-ylmethyl)-cyclopentyl-methyl-amine. Diagnostic 1H NMR (400 MHz, CDCl3) 1.40–1.90 (m, 4H), 2.15 (s, 3H), 2.78–2.89 (m, 1H), 3.56 (s, 2H), 7.29 (d, 1H, J=8.3 Hz), 7.70–7.80 (m, 1H), 8.28 (d, 1H, J=2.1 Hz); MS 225.3 (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-a5ad9533b9c647d282cdcab132e95a66
Source dataset
uspto-grants-2008_03
Patent number
US07345038B2

Reaction notes

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