Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-Methoxy-5-nitrophenol | HCID 69471 | — |
| Reactant | Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1) | HCID 77210 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 22496148 | HCID 22496148 | 91.2% |
Reaction Steps
2-methoxy-5-nitrophenol (254 mg, 1.5 mmol, 1 eq.) was placed in dimethylformamide (3 mL) with 4-(2-chloro-ethyl)morpholine hydrochloride (837 mg, 4.5 mmol, 3 eq.), Cs2CO3 (3.4 g, 10.7 mmol, 7 eq.), KI (547 mg, 3.3 mmol, 2.2 eq.). The reaction mixture was heated at 80° C. and stirred for 20 hours. The reaction mixture was then concentrated under reduced pressure and the resulting residue was diluted with ethyl acetate. The organic phase was washed with a 1% NaOH aqueous solution, dried over MgSO4, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel to afford 4-(2-(2-methoxy-5-nitrophenoxy)ethyl)morpholine (386 mg, 91%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09061999B2 |
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| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-b054c81b4ad547029a81665eb5b82ad7 |
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| Source note | uspto-grants-2015_06 |
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