Uses
N-Methylhex-5-en-1-amine can be used as a reagent to prepare quinazoline substituted cyclopentane and proline-urea based macrocycles as Hepatitis C virus (HCV) NS3/4A protease inhibitors.
Synthesis
The following step: To a reaction flask was added a methanol solution containing 25% methylamine in an amount of 10 equivalents of methylamine. Subsequently 1 equivalent of 6-bromo-1-hexene was added to the reaction flask and mixed with stirring. The reaction mixture was heated to 40°C in an oil bath and kept at this temperature for 3 hours. Upon completion of the reaction, the mixture was cooled to 20 °C and 0.1 equivalent of p-methoxyphenol was added as a stabilizer, along with 1 equivalent of sodium hydroxide. The excess methylamine methanol solution was recovered under negative pressure. Next, the mixture was heated to 50 °C and a colorless liquid product, N-methyl-5-hexen-1-amine, was obtained by distillation under reduced pressure. The yield of this step was 67% and the purity of the product was 96.5%.
References
[1] Patent: CN108003037, 2018, A. Location in patent: Paragraph 0014-0028
[2] Bulletin de la Societe Chimique de France, 1975, p. 2315 - 2320
