Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-Morpholinecarbonyl chloride | HCID 84810 | — |
| Reactant | HCID 18403905 | HCID 18403905 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | Acetonitrile methylene chloride | HCID 21877088 | — |
| Product | HCID 69677511 | HCID 69677511 | 75% |
Reaction Steps
To a solution of 2-methoxy-4-[2-(4-pyridin-2-yl-piperazin-1-yl)ethyl)phenol (1.5 g) and cesium carbonate (1.6 g) in 25% acetonitrile/dichloromethane was added 4-morpholinecarbonyl chloride (1.4 g), with stirring, under nitrogen. The reaction mixture was stirred for 18 hrs under nitrogen, diluted with ethyl acetate, and the layers were separated. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated. The residue was flash chromatographed (silica), eluting with 2% methanoludichloromethane. The appropriate fractions were collected and concentrated. The residue was dissolved in ethyl acetate and ethereal hydrochloride was added. The precipitate was collected and recrystallized from ethyl ethanol/ether to give 0.9 g (75%) of product, mp 185-186° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06479495B1 |
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| Source dataset | uspto-grants-2002_11 |
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| ORD ID | ord-8724e466a645458c99019d71ce7ecba0 |
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| Source note | uspto-grants-2002_11 |
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