Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Iodide | HCID 5238 | — |
| Reactant | 4-Fluorobenzyl chloride | HCID 9602 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Tert-butyl 3-amino-[1,1'-biphenyl]-4-carboxylate | HCID 58508425 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 68961266 | HCID 68961266 | 34.4% |
Reaction Steps
To N,N-dimethylformamide 0.5 mL solution of 4-fluorobenzyl chloride 35 mg were added tert-butyl 2-amino-4-phenylbenzoate 54 mg and potassium carbonate 55 mg at room temperature, and it was stirred at 80° C. for 11 hours. After the reaction mixture was cooled to room temperature, sodium iodide 30 mg was added to it at room temperature, and it was stirred at 80° C. for 4 hours and 40 minutes. After the reaction mixture was cooled to room temperature, ethyl acetate and 1.0 mol/L hydrochloric acid were added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Fuji SILYSIA Chemical Ltd., PSQ100B(spherical type), eluent; hexane:ethyl acetate=100:1] to give tert-butyl 2-(4-fluorobenzylamino)-4-phenylbenzoate 26 mg of a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08327467B2 |
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| Source dataset | uspto-grants-2012_12 |
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| ORD ID | ord-c88e128451c44897b300713fa337ad4b |
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| Source note | uspto-grants-2012_12 |
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