Extracurricular laboratory: Synthetic route of 51-06-9

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Amino-N-(2-diethylaminoethyl)benzamide, and friends who are interested can also refer to it.

Adding a certain compound to certain chemical reactions, such as: 51-06-9, name is 4-Amino-N-(2-diethylaminoethyl)benzamide, belongs to amides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 51-06-9, Computed Properties of C13H21N3O

Example V 4-[(Butylsulfonyl)amino]-N-[2-(diethylamino)ethyl]benzamide hydrobromide To 100 ml of methylene chloride add 6.52 g (36.2 mmole) of 4-amino-N-[2-(diethylamino)ethyl]benzamide and cool to -78 C. under nitrogen atmosphere. To this solution slowly add 5.61 g (36.2 mmole) of n-butanesulfonyl chloride. When the addition is complete, allow the reaction mixture to warm to room temperature and monitor by thin layer chromatography on silica gel (acetonitrile:ammonium hydroxide, 9:1). Upon completion of the reaction remove the solvent in vacuo. To the resulting oil add 50 ml H2 O followed by 50% sodium hydroxide until pH=14. Extract the aqueous layer with 3*50 ml diethyl ether and 2*25 ml of methylene chloride. To the aqueous layer add concentrated HCl to bring the pH to 8.5. Extract the aqueous solution with 3*75 ml of methylene chloride. Combine the extracts and dry over sodium sulfate. Filter the drying agent and remove the solvent in vacuo. Dissolve the resulting oil in acetonitrile. Bubble HBr gas through the solution until pH=1. Remove the solvent in vacuo. Triterate the resulting oil in diethyl ether and ethyl acetate to yield a precipitate. Isolate by filtration and recrystallize from MeOH/ethyl acetate to afford the title compound. NMR (DMSO-d6): delta=0.82(t,3), 1.22(t,6), 1.34(m,2), 1.63 (m,2), 3.23(m,8), 3.57(m,2), 7.26 (d,2), 8.67(t,1), 9.22(br s,1) and 10.19(s,1)ppm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Amino-N-(2-diethylaminoethyl)benzamide, and friends who are interested can also refer to it.

Reference:
Patent; Schering A.G.; US4544654; (1985); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics