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Synthesis and characterization of several local anaesthetics

Alnadeesh, Faten Mohammed Hezam (2013) Synthesis and characterization of several local anaesthetics. Masters thesis, Universiti Teknologi Malaysia, Faculty of Science.



Three local anaesthetics, tetracaine, lidocaine and benzocaine were synthesized and characterized. Tetracaine or 2-(diethylamino)ethyl 4-butylaminobenzoate was synthesized using two approaches. The first approach was a direct esterification of 4-butylaminobenzoic acid with 2-(diethylamino)ethanol in the presence of boron trifluoride etherate as catalyst to afford 2-(diethylamino)ethyl 4-butylaminobenzoate. The second approach involved two step reactions. Treatment of 4-butylaminobenzoic acid with ethanol in the presence of boron trifluoride etherate afforded ethyl 4-butylaminobenzoate in the first step, followed by, transesterification of ethyl 4-butylaminobenzoate with 2-(diethylamino)ethanol to afford 2-(diethylamino)ethyl 4-butylaminobenzoate in the second step. Lidocaine or 2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide was synthesized from 2,6-dimethylaniline, a-chloroacetyl chloride, diethylamine, with a-chloro-2,6-dimethylacetanilide being intermediate in the synthesis. Benzocaine or ethyl-4-aminobenzoate was synthesized by Fischer esterification of 4-aminobenzoic acid with absolute ethanol. The intermediates and products were characterized by using infrared (IR), proton nuclear magnetic resonance (1H NMR), and carbon nuclear magnetic resonance (13C NMR) spectroscopies.

Item Type:Thesis (Masters)
Additional Information:Thesis (Sarjana Sains (Kimia)) – Universiti Teknologi Malaysia, 2013; Supervisor : Prof. Dr. Hasnah Mohd. Sirat
Uncontrolled Keywords:anesthetics, local anesthetics
Subjects:Q Science > QD Chemistry
ID Code:38440
Deposited On:26 May 2014 08:46
Last Modified:19 Sep 2017 12:13

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