Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Methylamine | HCID 6329 | — |
| Edukt | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Edukt | 1-Phenylcyclopropanecarboxylic acid | HCID 80206 | — |
| Edukt | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Lösungsmittel | Methanol | HCID 887 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Produkt | 1198225-51-2 | HCID 58168711 | 34,1% |
Reaktionsschritte
1-Phenylcyclopropanecarboxylic acid (2.95 g) was dissolved in DMF (120 mL). To the solution, EDC.HCl (5.2 g), HOBt (3.2 g), and a solution of methylamine in methanol (40%, 1.94 mL) were added, and the mixture was stirred at room temperature for 5 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (50% ethyl acetate/hexane). An aliquot (1.1 g) of the obtained amide compound (2.9 g) was dissolved in THF (60 mL). To the solution, a solution of LAH in THF (2.4 M, 7.9 mL) was added dropwise at 0° C., and the mixture was heated to reflux at 80° C. for 12 hours. To the reaction mixture, water (4.0 mL) was gradually added dropwise at 0° C. The precipitate was removed by filtration and washed with THF (60 mL). Then, the combined filtrate was concentrated under reduced pressure to obtain the title compound (1.0 g) as a colorless oil.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US08530490B2 |
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| Quelldatensatz | uspto-grants-2013_09 |
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| ORD ID | ord-f6bc5e03c5a04fc3b945c958532c1f0d |
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| Quellennotiz | uspto-grants-2013_09 |
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