N-Methylcyclohexylamine → (6-Chloro-pyridin-3-ylmethyl)-cyclohexyl-methyl-amine

HRID 1392913

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[CH2:17][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[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH3:10])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-chloro-5-(chloromethyl)pyridine (500 mg, 3.08 mmole) in 8 mL of dry acetonitrile is 384 mg (3.39 mmol) of N-methylcyclohexylamine followed by 468 mg (3.39 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 700 mg (95% yield) of (6-Chloro-pyridin-3-ylmethyl)-cyclohexyl-methyl-amine. C13 NMR 26.1, 26.6, 28.9, 37.7, 54.5, 62.8, 124.1, 135.1, 139.5, 149.9; MS 239.3 (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-bfdb167232b440dbae80b39d59a87147
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07345038B2

Linked notes

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