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Reaction id: 0501011055_35, verified by Personal Chemistry ©
20c
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4
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TMS-Cl
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MeCN
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21c
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Yield: 96% Time: 600s Temperature: 150 °C
Chemicals
| Name |
MW [g/mol] |
Density [g/ml] |
Amount [mmol] |
Mass/Volume |
| Substrate 1 |
109.128 |
1.000 |
0.600 |
65.477 µl |
| 461-58-5 |
84.082 |
1.000 |
0.607 |
51.000 mg |
| TMS-Cl (2.0M in MeCN) |
108.644 |
1.000 |
0.660 |
330.000 µl |
| MeCN |
41.053 |
0.780 |
15.200 |
800.000 µl |
| Product 1 |
229.671 |
1.000 |
0.000 |
0.000 µl |
Keywords
Addition, Amination
Comments
Synthesis: Using this acid (HCl or TMS-Cl) catalysed method, a library of 60 compounds was synthesised. Optimisation (of solvent, acid catalyst, time, temperature and concentrations) was carried out to find the best yields and a method where the products would precipitate and be easily separated and isolated. Addition of the acid (in acetonitrile) to the reaction mixture was done automatically by the Synthesizer system.
Work-up and purification: After heating of the reaction mixture, 138 µl isopropanol was added and the mixture stirred for 10 s and heated once more, to 125°C for 30 s. After the second heating, the product hydrochloride was filtered off and washed twice with acetonitrile.
Characterisation: By LCMS, 1H and 13C NMR.
Instrument Settings
Absorption level: Normal
Pre-stirring time: 0s
References
Mayer, S.; Daigle, D. M.; Brown, E. D.; Khatri, J.; Organ, M. G. J. Comb. Chem. 2004, 5, 776-782
Analysis
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