N,N,N',N'-Tetramethylethylenediamine → HCID 19028011, compound

Temperature

0 °C

7.61 g of 3,5-dimethoxytoluene and 6.10 g of tetramethylethylenediamine are dissolved under nitrogen in 150 ml of hexane. The solution is cooled to 0° C., 32.8 ml of 1.6 M butyllithium in hexane are added and the mixture is stirred at 10° C. for 20 minutes and then at 20° C. for 1 hour. To the lithium derivative cooled to -10° C., a solution, cooled to 0° C., of 6.13 g of N-methoxy-N-methylchloroacetamide in 50 ml of THF is added in the course of 20 minutes. The reaction mixture is left for one hour at a temperature of between 0° and 5° C. and for one hour at 20° C., and then poured into 100 ml of water. The resulting mixture is extracted with twice 300 ml of diethyl ether, the ether phases are washed with saturated sodium chloride solution, and the organic phases are dried over magnesium sulphate, filtered and concentrated under vacuum. The residue is chromatographed on silica, eluting with a DCM/hexane (50:50; v/v) mixture. Concentration of the pure fractions yields 1.6 g of the expected product; m.p. 82°-84° C.

1. waitat 20° C. for 1 hour
2. additionis added in the course of 20 minutes
3. waitThe reaction mixture is left for one hour at a temperature of between 0° and 5° C. and for one hour at 20° C.
4. extractionThe resulting mixture is extracted with twice 300 ml of diethyl ether
5. washthe ether phases are washed with saturated sodium chloride solution
6. dry with materialthe organic phases are dried over magnesium sulphate
7. filtrationfiltered
8. concentrationconcentrated under vacuum
9. customThe residue is chromatographed on silica
10. washeluting with a DCM/hexane (50:50; v/v) mixture

ORD record

ord-e685188bfd91432aa5f8bb80eadf8ada

Source dataset

uspto-grants-1997_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05656648