Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Morpholine | HCID 8083 | — |
| Reactant | Sulfuric acid magnesium salt (1:1) | HCID 24083 | — |
| Reactant | 1-(9-Ethyl-6-(4-fluorobenzoyl)-9H-carbazol-3-yl)ethanone | HCID 68452867 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Solvent | Ethyl acetate hexane | HCID 21226206 | — |
| Product | HCID 68452677 | HCID 68452677 | 21.5% |
Reaction Steps
To 1-[9-Ethyl-6-(4-fluoro-benzoyl)-9H-carbazol-3-yl]-ethanone (1.30 g; 25.6 mmol) in N,N-Dimethylacetamide (DMA) (10 ml) is added morpholine (1.07 g; 12.3 mmol) at 100° C. This reaction mixture is stirred at 140° C. for 15 h. After the reaction is completed, the reaction mixture is poured into H2O, then, a beige solid was obtained by filtration. The solid is dissolved in CH2Cl2, followed by dying over anhydrous MgSO4. Condensation under reduced pressure affords a beige solid as crude product. (1.13 g) The pure product was obtained by silica gel column chromatography with ethylacetate/hexane (1/3-1/1) as eluent. (1.03 g, 67%). The structure is confirmed by the 1H-NMR spectrum (CDCl3). δ[ppm]: 1.50 (t, 3H), 2.72 (s, 3H), 3.36 (t, 4H), 3.89 (t, 4H), 4.44 (q, 2H), 6.96 (d, 2H), 7.48 (dd, 2H), 7.86 (dd, 2H), 8.05 (dd, 1H), 8.16 (dd, 1H), 8.58 (d, 1H), 8.73 (d, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07759043B2 |
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| Source dataset | uspto-grants-2010_07 |
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| ORD ID | ord-7aac4d0fe5194b139eec3763e762d29e |
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| Source note | uspto-grants-2010_07 |
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