Azepane → 1-[(6-Chloropyridin-3-YL)methyl]azepane

HRID 1392908

Reaction equation

HRID 1392908 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][N:3]=1.[NH:10]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][N:10]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8119AzepaneHCID 11430Potassium CarbonateHCID 1554792-Chloro-5-(chloromethyl)pyridine

Product 1

HCID 201154641-[(6-Chloropyridin-3-YL)methyl]azepaneYield 59%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-chloro-5-(chloromethyl)pyridine (419 mg, 2.59 mmole) in 5 mL of dry acetonitrile is 512 mg (5.18 mmol) of azacycloheptane followed by 358 mg (2.59 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 (59% yield) of 1-(6-Chloro-pyridin-3-ylmethyl)-azepane. Diagnostic 1H NMR (400 MHz, CDCl3) 1.40–1.70 (m, 8H), 2.50–2.65 (m, 4H), 3.65 (s, 2H), 7.28 (d, 1H, J=8.3 Hz), 7.65–7.70 (m, 1H), 8.30 (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-c4ddc8b6b54743bebd1f66ff46b4ba10
Source dataset
uspto-grants-2008_03
Patent number
US07345038B2

Linked notes

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