Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | o-Fluorobenzaldehyde | HCID 67970 | — |
| Reactant | 3-[(4′-Chloro[1,1′-biphenyl]-4-yl)methoxy]piperidine | HCID 58992655 | — |
| Catalyst | Tetrabutylammonium Iodide | HCID 67553 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86615888 | HCID 86615888 | 53% |
Reaction Steps
Tetrabutylammonium iodide (26.9 mg, 0.0729 mmol) and potassium carbonate (206 mg, 1.46 mmol) were added to a solution of 3-[(4′-chlorobiphenyl-4-yl)methoxy]piperidine (220 mg, 0.729 mmol) and 2-fluorobenzaldehyde (0.159 mL, 1.46 mmol) in N,N-dimethylformamide (5 mL). The mixture was stirred at 100° C. for 8 hours. Subsequently, water was added and the mixture was extracted with ethyl acetate and washed with brine. The washed product was dried over magnesium sulfate and the solvent was evaporated. Purification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=40:1->10:1) gave 156 mg (53%) of the desired compound as a pale yellow powder.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07902367B2 |
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| Source dataset | uspto-grants-2011_03 |
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| ORD ID | ord-aa0b40b1bb7545c387930c3dda8f5de9 |
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| Source note | uspto-grants-2011_03 |
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