I'm trying to synthesize amides from a bipyridine (carboxylic acid) and an aromatic amine.
HCL,EDCI and N, N- diisopropylethylamine react with a solution of biphenyl-2-yl-carbamic acid 1-{2- [4-(2-amino-ethyl)-phenyl}-ethyl}-piperidin-4-yl ester , 2-fluoro-4- hydroxybenzoic acid and HOBt in dimethylformamide and stirred for 24 hours at room temperature under nitrogen. The solvent was removed in vacuo and the residue purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia, 97:3:0.3 to 95:5:0.5 (by volume), to furnish the title compound as a white foam, 95% yield, 3.08 g.
The best reagent for amide synthesis is T3P. This is available as solution in ethyl acetate. The reaction procedure is so simple and the by product is water soluble which makes the purification easy. If you can afford to buy T3P, try this and I am sure that you would enjoy this reagent
Felipe,
The procedure mentioned above by Emmanuvel seems to be a good one by using n-propylphosphonic anhydride (T3P) in presence of N-methylmorpholine(Base) and CH3CN(Solvent). See
---Chilakapati Madhu et al., Int J Pept Res Ther (2014). DOI 10.1007/s10989-013-9383-7.
Good luck
There is also the T3P version in DMF, if you SMs are not soluble in EtOAc.
The standard procedure for amidation is to treat acyl halide with ammonia.
Prepare insitu acid chloride /or mixed anhydride& condense with amine
Schotten-Baumann reaction; can even be used for continuous flow conditions
- Badges
- Science topic
- Similar topics
- Chemistry
- Organic Chemistry