Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 1-Ethylpiperazine | HCID 79196 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 6-Chloro-3-pyridinecarbonitrile | HCID 5152094 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 889851-56-3 | HCID 16748394 | 46.2% |
Reaction Steps
A mixture of 2 g (14 mmol) 6-chloronicotinonitrile (commercially available) and 0.88 g (7 mmol) N,N-diisopropylethylamine in 20 ml water and 4 ml DMF was heated to 80° C. During 2 min 1.98 g (17 mmol) N-ethylpiperazine was added and stirred at 80° C. for 1 h. 100 ml 1M aq. Na2CO3 solution was added and the mixture was extracted three times with 100 ml ethyl acetate each. The combined organic phases were washed twice with 100 ml brine each and dried with MgSO4. After evaporation the residue was purified with flash chromatography on Alox eluting with a gradient of ethyl acetate/heptan to yield 1.4 g (45%) of the title compound as slightly yellow crystals. (m/e): 21702 (MH+; 100%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07528135B2 |
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| Source dataset | uspto-grants-2009_05 |
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| ORD ID | ord-0c4741cb8e974cf58fc30d685734674e |
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| Source note | uspto-grants-2009_05 |
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