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ChemicalBook CAS DataBase List N,N'-Diemthyl-N-Methyllisonipecotamide
613678-09-4

N,N'-Diemthyl-N-Methyllisonipecotamide synthesis

1synthesis methods
-

Yield: 90%

Reaction Conditions:

with triethylamine in tetrahydrofuran at 0 - 20;

Steps:

5
Resuspend N-methylisonipecotyl chloride hydrochloride (489 g, 2.54 mol) in anhydrous THF (5000 mL) and cool the suspension to 0-5°C. Add a solution of dimethylamine in THF (2M, 2500 ml, 2eq. ) and triethylamine (775 g, 3eq. ) dropwise to the reaction mixture maintaining the temperature below 7°C. Stir the suspension for 3 hrs. at this temperature and then allow the reaction mixture to warm to 20°C overnight. Then cool the reaction mixture to 5°C and 30% NaOH (600 mL) and add CH2CI2 (2 L). Separate the organic layer from the sticky solid that is formed and redissolve the solid in water (2 L). Extract the solution with CH2CI2 (2 L). Combine the organic fractions, concentrate to about 3500 mL, and wash twice with water (500 mL). Dry the organic layer with Na2SO4, filter, and concentrate to dryness. Dry the red oil under vacuum at room temperature to produce the title product (378.7 g, 90 % yield). Treat with ether and evaporate to dryness to obtain the product as a solid.

References:

ELI LILLY AND COMPANY WO2003/84949, 2003, A1 Location in patent:Page/Page column 46; 47

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