Hydrochloric Acid → Methyl 4-((methylamino)methyl)benzoate hydrochloride

To 12.2 g of the compound obtained in step (1-2) above was added 20 ml of an ethyl acetate solution of 4N hydrochloric acid under ice-cooling and after stirring the mixture for one hour, the crystals formed were collected by filtration to provide 6.8 g (yield 90%) of 4-(N-methylaminomethyl)benzoic acid methyl ester hydrochloride. Then, 6.5 g of the crystals thus obtained was dissolved in 30 ml of DMF and 4.2 ml of triethylamine and 5.0 g of (S)-2-methylbutyl bromide were added to the solution under ice-cooling. Then, 1.3 g of 60% sodium hydride was added little by little to the solution and the mixture was heated to 80° C. for from 1 to 2 hours. After cooling, the reaction mixture was diluted with 80 ml of diethyl ether and 5 ml of purified water was added dropwise slowly to the solution. The organic layer formed was collected and, after successively being washed with 20 ml of purified water, 20 ml of a saturated aqueous sodium hydrogen carbonate solution, and then 20 ml of a saturated aqueous sodium chloride solution, dried with magnesium sulfate, and then the solvent was distilled off under reduced pressure.

1. temperaturecooling
2. customthe crystals formed
3. filtrationwere collected by filtration

ORD record

ord-71c0c30d2b144014a67d41e3c6ec00e6

Source dataset

uspto-grants-1992_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05166403