Piperidine → 2-chloro-5-(piperidin-1-ylmethyl)pyridine

HRID 1392916Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-chloro-5-(chloromethyl)pyridine (578 mg, 3.57 mmole) in 7 mL of dry acetonitrile is added 0.71 mL (7.14 mmol) of piperdine followed by 493 mg (3.57 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 581 mg (77% yield) of 2-Chloro-5-piperidin-1-ylmethyl-pyridine. Diagnostic 1H NMR (400 MHz, CDCl3) 1.40–1.65 (m, 6H), 2.20–2.39 (s, 4H), 3.47 (s, 2H), 7.28 (d, 1H, J=7.9 Hz), 8.60–8.69 (m, 1H), 8.28 (d, 1H, J=2.1 Hz); MS 211.3 (M+H).

Workup

temperatureAfter cooling
customthe reaction mixture is quenched with 5 mL of water
extractionextracted three-times with methylene chloride
dry with materialdried over sodium sulfate
customConcentration of the solvent provided an oil which
customwas purified by silica gel chromatography

Sources & evidence

ORD record: ord-f0c73504e4954e7d831d9ec1e2301ca3
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07345038B2

Reaction notes

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