Potassium Carbonate → HCID 9964264, compound

HRID 1392904Notes

Reaction equation

HRID 1392904 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][N:3]=1.Cl.[NH:11]1[CH2:14][CH2:13][CH2:12]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]2[CH2:14][CH2:13][CH2:12]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 12308726Azetidine hydrochloride

Product 1

HCID 9964264HCID 9964264, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-chloro-5-(chloromethyl)pyridine (0.34 g, 2.1 mmole) in 4 mL of dry acetonitrile is 389 mg (4.14 mmol) of azetidine-hydrochloride followed by 572 mg (4.14 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 200 mg (53% yield) of 1-(6-Chloro-pyridin-3-ylmethyl)-azetidine. Diagnostic 1H NMR (400 MHz, CDCl3) 2.06–2.14 (m, 2H), 3.23 (t, 4H, J=7.0 Hz), 3.55 (s, 2H), 7.27 (d, 1H, J=7.9 Hz), 7.61 (dd, 1H, J=8.3 and 2.5 Hz), 8.26 (d, 1H, J=2.5 Hz); MS 183.2 (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-00f2ab62a2024d2faefa300bd8d5c4a9
Source dataset
uspto-grants-2008_03
Patent number
US07345038B2

Reaction notes

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