Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Phenethylamine | HCID 1001 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | L-Proline | HCID 145742 | — |
| Reactant | HCID 57667811 | HCID 57667811 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 57667997 | HCID 57667997 | — |
Reaction Steps
To dimethylsulfoxide 2.0 mL solution of 2-iodo-4-phenethylbenzoic acid 0.20 g were added phenethylamine 0.11 mL, copper (I) iodide 0.010 g, proline 0.013 g and potassium carbonate 0.16 g, and it was stirred at 60° C. for 4 hours. After the reaction mixture was cooled to room temperature, 1.0 mol/L hydrochloric acid and ethyl acetate 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:acetic acid=90:10:1] to give 4-phenethyl-2-(phenethylamino)benzoic acid 0.12 g of white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08327467B2 |
|---|
| Source dataset | uspto-grants-2012_12 |
|---|
| ORD ID | ord-5232c4d769564b96bad2264d7d53b74b |
|---|
| Source note | uspto-grants-2012_12 |
|---|
