SYNTHESIS OF 1-(1,3-BENZODIOXANE-6-YL)-2-TERT- BUTYLAMINEOETHANONE AS A PRECURSOR TO ASTHMA DRUGS SALBUTAMOL

• Main Author: Novia Yussanti, Azizah
• Format: Final Project
• Language: Indonesia
• Subjects: Kimia
• Online Access: https://digilib.itb.ac.id/gdl/view/75143
• Institution: Institut Teknologi Bandung

Salbutamol is one of the drugs used to treat respiratory diseases in humans, especially asthma. This compound has been successfully synthesized by various reactions and precursors. In this study, the precursor compound of salbutamol was 1-(1,3-benzodioxane- 6-yl)-2-tert-butylaminoethanone (8). In addition, this study has succeeded in optimizing and increasing the scale of the reaction of 6-acetyl-1,3-benzodioxane (3) and 6- bromoacetyl-1,3-benzodioxane (6) by using a simpler reaction step and in accordance with the principles of green chemistry. The synthesis of the compound 1-(1,3-benzodioxane-6- yl)-2-tert-butylaminoethanone (8) includes three reaction stages, namely the formation of dioxane groups to p-hydroxyacetophenone precursor through hydroxy methylation reactions using paraformaldehyde in an acidic solvent, bromination reactions , and amination reactions. The compound 6-acetyl-1,3-benzodioxane (3) as a result of the reaction products of the first stage was obtained with a yield of 30.30% and 34.95% with a mole ratio of p-hydroxyacetophenone and paraformaldehyde 1 : 7 and 1 : 14 respectively. Bromination reaction stage was carried out on the compound with two different reagents, namely Br2 and PyHBr3. The brominated compound product was 6-bromoacetyl-1,3- benzodioxane (6) with the highest yield of 61.26%. The amination of the brominated product produced 1-(1,3-benzodioxane-6-yl)-2-tert-butylaminoethanone (8) with a yield of 56.98%. The products of the three reaction stages were characterized using 1H-NMR and 13C-NMR. Based on these measurements, intermediate compounds and target compounds have been successfully synthesized.