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Reaction id: 0501011058_01, verified by Personal Chemistry ©
1a
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Piperidine
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ps-BEMP
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MeCN
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1a (1)
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Yield: 57% Time: 900s Temperature: 200 °C
Chemicals
| Name |
MW [g/mol] |
Density [g/ml] |
Amount [mmol] |
Mass/Volume |
| Substrate 1 |
204.072 |
1.000 |
0.980 |
200.000 µl |
| 110-89-4 |
85.150 |
0.861 |
9.800 |
969.187 µl |
| ps-BEMP (2.2 mmol/g, polystyrene) |
273.385 |
1.000 |
0.990 |
450.000 mg |
| MeCN |
41.053 |
0.780 |
9.500 |
500.000 µl |
| Product 1 |
208.305 |
1.000 |
0.000 |
0.000 µl |
Keywords
Amination, Heterocyclic, N-Arylation, Nucleophilic aromatic substitution, Solid supported, Substitution
Comments
Synthesis: In order to find a method for amination of 3-bromoisoxazoles, different reaction conditions were tested. No product was formed using conventional heating (with DMAP, KOH or Ag2CO3 for 72-120 hours). Using ps-BEMP (2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine) and microwave heating, 57% of the desired product could be isolated. Solution phase BEMP reactions could only be heated to 180°C, at higher temperatures the pressure in the reaction vial was too high.
Work-up and purification: After the reaction, the polystyrene-supported BEMP was filtered off and the filtrate concentrated under reduced pressure. The product was isolated using flash chromatogaphy (silica eluted with heptane:ethyl acetate: triethylamine 4:1:0.1).
Characterisation: By 1H NMR, 13C NMR, IR and HRMS.
Instrument Settings
Absorption level: High
Pre-stirring time: 0s
References
Moore, J. E.; Spinks, D.; Harrity, J. P. A. Tet. Lett. 2004, 16, 3189-3191
Analysis
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