Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-Chloro-3-nitrophenol | HCID 69127 | — |
| Reactant | 4-(2-chloroethyl)piperidine | HCID 10487004 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 67974225 | HCID 67974225 | 56.1% |
Reaction Steps
4-chloro-3-nitrophenol (2.5 g, 14.4 mmol, 1 eq.) was placed in dimethylformamide (48 mL) with 4-(2-chloro-ethyl)piperidine (8 g, 43.2 mmol, 3 eq.), Cs2CO3 (33 g, 100.8 mmol, 7 eq.), KI (5.3 g, 31.7 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-(4-chloro-3-nitrophenoxy)ethyl)piperidine (2.3 g, 56%).
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-f293ecc095c44665ad213e3c7bd45480 |
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| Source note | uspto-grants-2015_06 |
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