Nisoxetine synthesis
- Product Name:Nisoxetine
- CAS Number:53179-07-0
- Molecular formula:C17H21NO2
- Molecular Weight:271.36
Yield:53179-07-0 0.11 g
Reaction Conditions:
with tetra-(n-butyl)ammonium iodide;potassium carbonate in methanol at 80; for 24 h;Sealed tube;
Steps:
N-Methyl or N,N-dimethyl 3-phenyl-3-aryloxy-1-propylamines or 4-phenyl-4-aryloxy-1-butylamines(1, 2, 7-11).
General procedure: A slurry of the appropriate (3-chloro-1-aryloxypropyl)benzene or (4-chloro-1-aryloxybutyl)benzene (approx. 0.5 mmol), tetrabutylammonium iodide (0.037 g, 0.1 mmol) and potassiumcarbonate (0.27 g, 2 mmol) in a solution of N-methylamine or N,N-dimethylamine (2.0M in methanol, 4 mL,8 mmol) was heated in a sealed tube for 24 hours. After cooling in an ice bath the white slurry was poured into water (30 mL) and extracted with ethyl acetate (3 x 25 mL). The combined organic phases were pooled, dried over sodium sulphate, filtered, and evaporated. The product was purified by flash chromatography through a short plug of silica by means of triethylamine-ethyl acetate (1:4) followed by evaporation andbulb-to-bulb distillation.
References:
Andersen, Jacob;Stuhr-Hansen, Nicolai;Zachariassen, Linda Gronborg;Koldso, Heidi;Schiott, Birgit;Stromgaard, Kristian;Kristensen, Anders S. [Molecular Pharmacology,2014,vol. 85,# 5,p. 703 - 714] Location in patent:supporting information
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