Aminoacetaldehyde dimethyl acetal

Description

Aminoacetaldehyde dimethyl acetal, also referred to as 2,2-dimethoxy-ethylamine, is a key intermediate in the chemical synthesis of various pharmaceuticals and raw materials. It plays a crucial role in the production of ivabradine hydrochloride, proline analogs, praziquantel, and other compounds.

The current industrial process for synthesizing aminoacetaldehyde dimethyl acetal begins with vinyl acetate as the starting material. The synthesis of the target product involves several steps, including bromination, Gabriel synthesis, and hydrazinolysis, which collectively contribute to the formation of this important intermediate.

Chemical properties

clear colorless to pale yellow liquid

What are the applications of Application

Amino acetaldehyde dimethyl was used in preparation of chitosan- dendrimer hybrids having various functional groups such as carboxyl, ester and poly(ethylene glycol). It was used in an synthesis of a bicyclic proline analog from L-ascorbic acid and in 3-component reaction catalyzed by MgClO4 leading to α-aminophosphonates.

General Description

Aminoacetaldehyde dimethyl acetal reacts with sulfone, followed by hydrolysis and reductive amination by adding desired piperazine derivative to yield piperazine derivatives of 2-furanyl[1,2,4]triazolo[1,5-a][1,3,5]triazine.

Aminoacetaldehyde dimethyl acetal is used as a building block for the synthesis of various acylated and sufonylated oxyenamides.

Purification Methods

Dry the acetal over KOH pellets and distil it through a 30cm vacuum jacketed Vigreux column (p 11). [Lawson J Am Chem Soc 75 3398 1953, Erickson et al. J Am Chem Soc 77 6640 1955, Beilstein 4 IV 1918.]