3-(3-iodopropyl)-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one CAS:148870-57-9

The synthesis of 3-(3-iodopropyl)-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one can be achieved through a series of organic reactions starting from a suitable aromatic precursor, such as an aniline. The first step involves the protection of the amino group in aniline to prevent its involvement in unwanted side reactions during subsequent steps. This can be done using a protecting group such as a carbamate or sulfonamide. Next, the aniline derivative is subjected to a nitration reaction to introduce a nitro group at the desired position on the benzene ring. A nitrating agent such as a mixture of nitric acid and sulfuric acid is typically used for this purpose. After nitration, the nitro group is reduced to an amino group using a reducing agent such as iron or tin in the presence of hydrochloric acid. This step results in the formation of aniline derivative with an amino group at the desired position. The aniline derivative is then cyclized to form the benzazepine ring. This can be achieved through intramolecular condensation reactions, such as the Friedlander reaction, where the amino group attacks the carbonyl group of a suitably substituted benzaldehyde, followed by dehydration to form the ring. Finally, the iodoalkyl chain is introduced into the 3 position of the azepine ring through a nucleophilic substitution reaction using an iodoalkyl halide and a suitable base. This step results in the formation of 3-(3-iodopropyl)-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one. 3-(3-Iodopropyl)-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one is a valuable intermediate in organic synthesis, finding applications in the preparation of various pharmaceuticals and other organic compounds. The presence of the iodoalkyl chain and the methoxy groups make it a versatile building block for the synthesis of more complex molecules. The compound can be further modified or functionalized to create more complex molecules with improved pharmacological properties.