Dimethyl Sulfate → HCID 19387890, compound

Participants

Reaction Conditions

Reaction Steps

Example P-13:1.3 g of 7-(1-aminoethyl)-1,2,3,4-tetrahydro-quinoline, 0.73 gof dimethyl sulfate and 0.27 g of ground magnesium oxide in 50 ml of absolute toluene are placed in a sulfonation flask. The internal temperature is then increased to 100°-105° C. and the mixture is stirred at that temperature for 18 hours. After cooling, inorganic material is filtered off, 10 ml of cone. HCl are added to the toluene solution, and the batch is maintained at 70° C. for 2 hours. The batch is then neutralised with sodium hydroxide solution and the organic phase is removed. The aqueous phase is subsequently further extracted twice with ethyl acetate and the organic phases are dried over Na2SO4. After removal of the solvent under a water-jet vacuum, 1.2 g of crude product are obtained which can be purified by flash chromatography on silica gel (eluant: ethyl acetate/n-hexane 1: 1) to yield 1.05 g of 7-(1-aminoethyl)-1-methyl-1,2,3,4-tetrahydro-quinoline in the form of a red oil (1H-NMR).

Provenance & Evidence