Dimethylamine → 1-(6-Chloropyridin-3-yl)-N,N-dimethylmethanamine
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][CH3:12].C(=O)([O-])[O-].[K+].[K+].O>C(O)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][N:11]([CH3:12])[CH3:10])=[CH:6][CH:7]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
2-Chloro-5-(chloromethyl)pyridine (500 mg) was dissolved in ethanol (7.0 ml). dimethylamine (0.83 ml, 33% in ethanol) and potassium carbonate (641 mg) were added and the resulting mixture was refluxed for 1.5 hours. After evaboration of ethanol, water was added and the aqueous mixture was extracted with ethyl acetate. 1H NMR (400 MHz, d6-DMSO) δ: 8.31 (d, 1H, J 2.3 Hz), 7.77 (dd, 1H, J 8.2, 2.3 Hz), 7.47 (d, 1H, J 8.2 Hz), 3.41 (s, 2H), 2.14 (s, 6H).
Workup
- temperaturethe resulting mixture was refluxed for 1.5 hours
- extractionthe aqueous mixture was extracted with ethyl acetate
Sources & evidence
- ORD record
- ord-a72f5db53d9240e08e12fcd5aba29a27
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07482340B2
Reaction notes
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