Triethylamine → HCID 59164566, compound

To a solution of 5.20 g 3-(4-Cyano-3-methyl-phenyl)-propionic acid and 4.57 ml triethylamine in 100 ml tert-butanol 9.10 g diphenylphosphorylazide were given and the mixture heated under reflux overnight. The cooled reaction mixture was evaporated in vacuo. The resulting residue was dissolved in 150 ml ethyl acetate, washed with 50 ml citric acid/brine=1:1 and 50 ml saturated NaHCO3 solution and then dried over MgSO4. The residue was dissolved in 50 ml dichloromethane and 20 ml trifluoroacetic acid were added. The reaction mixture was stirred at room temperature for two hours. The solvent was removed in vacuo. The residue was coevaporated four times with portions of 100 ml toluene. The resulting brown residue was taken up in 50 ml acetonitrile and stirred at room temperature. The solid material was filtered off and dried in vacuo to obtain 2.45 g 4-(2-Amino-ethyl)-2-methyl-benzonitrile as its trifluoroacetate salt. The filtrate was evaporated in vacuo, the resulting residue was taken up in 100 ml diethyl ether and stirred at room temperature. The solid material was filtered off and dried in vacuo to obtain 1.17 g 4-(2-Amino-ethyl)-2-methyl-benzonitrile as its trifluoroacetate salt.

1. temperaturethe mixture heated
2. temperatureunder reflux overnight
3. customThe cooled reaction mixture
4. customwas evaporated in vacuo
5. dissolutionThe resulting residue was dissolved in 150 ml ethyl acetate
6. washwashed with 50 ml citric acid/brine=1:1 and 50 ml saturated NaHCO3 solution
7. dry with materialdried over MgSO4
8. dissolutionThe residue was dissolved in 50 ml dichloromethane
9. addition20 ml trifluoroacetic acid were added
10. customThe solvent was removed in vacuo
11. stirringstirred at room temperature
12. filtrationThe solid material was filtered off
13. customdried in vacuo

ORD record

ord-faf4648dfd444a3a9e5c6ab6bc2fbc83

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07655679B2