Cyclopropylamine → N-[(3,4-dimethoxypyridin-2-yl)methyl]cyclopropylamine
Reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.Cl.Cl[CH2:7][C:8]1[C:13]([O:14][CH3:15])=[C:12]([O:16][CH3:17])[CH:11]=[CH:10][NH+:9]=1.ClCCl.CO>C(O)C.C(=O)([O-])O.[Na+]>[CH3:15][O:14][C:13]1[C:8]([CH2:7][NH:4][CH:1]2[CH2:3][CH2:2]2)=[N:9][CH:10]=[CH:11][C:12]=1[O:16][CH3:17]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 58 °C
Procedure
1.05 ml (14.9 mmol) of cyclopropylamine was added to a solution of 695 mg (2.66 mmol) of 2-chloromethyl-3,4-dimethoxypyridinium hydrochloride in 4 ml ethanol and 4 ml of saturated aqueous sodium hydrogen carbonate. The reaction mixture was stirred for 1.5 hrs at 58° C. and extracted with ethyl acetate (3×10 ml). The combined organic layers were dried over magnesium sulphate and concentrated in vacuum. Column chromatography (gradient dichloromethane/methanol) yielded 263 mg (42% yield) of N-[(3,4-dimethoxypyridin-2-yl)methyl]cyclopropylamine.
Workup
- extractionextracted with ethyl acetate (3×10 ml)
- dry with materialThe combined organic layers were dried over magnesium sulphate
- concentrationconcentrated in vacuum
Sources & evidence
- ORD record
- ord-e049e3b9caea4c52b6ec0dd356be1a24
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07803821B2
Reaction notes
Loading…