Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Methyl 2-(bromomethyl)benzoate | HCID 2734813 | — |
| Reactant | HCID 53434390 | HCID 53434390 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | HCID 57949695 | HCID 57949695 | 46% |
Reaction Steps
A mixture of 2-bromomethyl-benzoic acid methyl ester (0.23 g, 1.0 mmol), 3-(3-trifluoromethoxy-phenyl)-propylamine (0.219 g, 1.0 mmol), and K2CO3 (0.25 g, 1.8 mmol) in toluene (10 mL) was heated with stirring at 100° C. for 2 h. Workup and silica gel column chromatography using 30% ethyl acetate in hexane afforded 2-[3-(3-trifluoromethoxy-phenyl)-propyl]-2,3-dihydro-isoindol-1-one (0.153 g, 46%). 1H NMR (300 MHz, CDCl3): δ (ppm) 2.02 (m, 2H), 2.72 (t, 2H), 3.69 (t, 2H), 4.36 (s, 2H), 7.02-7.56 (m, 7H), 7.84 (d, 1H). GC-MS: m/z 335 (M)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07968570B2 |
|---|
| Source dataset | uspto-grants-2011_06 |
|---|
| ORD ID | ord-74a87fc5b7894f4aa6f1eefa4803f01c |
|---|
| Source note | uspto-grants-2011_06 |
|---|