Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Methyl 2-(bromomethyl)benzoate | HCID 2734813 | — |
| Reactant | 3-(4-Chlorophenyl)propan-1-amine | HCID 6485772 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | HCID 57949603 | HCID 57949603 | 23% |
Reaction Steps
A mixture of 2-bromomethyl-benzoic acid methyl ester (0.115 g, 0.5 mmol), 3-(4-chloro-phenyl)-propylamine (0.102 g, 0.6 mmol), and K2CO3 (0.207 g, 1.5 mmol) in toluene (3 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-(4-chloro-phenyl)-propyl]-2,3-dihydro-isoindol-1-one (0.031 g, 23%). 1H NMR (300 MHz, CDCl3): δ (ppm) 1.96 (m, 2H), 2.69 (t, 2H), 3.64 (t, 2H), 4.36 (s, 2H), 7.14-7.58 (m, 7H), 7.84 (d, 1H). GC-MS: m/z 285 (M)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07968570B2 |
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| Source dataset | uspto-grants-2011_06 |
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| ORD ID | ord-4cb4041b23724f6c9b450fb016aa4d6c |
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| Source note | uspto-grants-2011_06 |
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