HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-(2,4-Dimethoxy-benzyl)-4-(2-dimethylamino-ethoxy)-2,3-dihydro-1H-isoindole → [2-(2,3-Dihydro-1H-isoindol-4-yloxy)-ethyl]-dimethyl-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-(2,4-Dimethoxy-benzyl)-4-(2-dimethylamino-ethoxy)-2,3-dihydro-1H-isoindole | HCID 59263107 | — |
| Solvent | Trifluoroacetic acid | HCID 6422 | — |
| Solvent | Anisole | HCID 7519 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | [2-(2,3-Dihydro-1H-isoindol-4-yloxy)-ethyl]-dimethyl-amine | HCID 46915187 | 242.4% |
Reaction Steps
A solution of 2-(2,4-dimethoxy-benzyl)-4-(2-dimethylamino-ethoxy)-2,3-dihydro-1H-isoindole (170 mg, 0.48 mmol) in trifluoroacetic acid (0.5 mL) and anisole (0.5 mL) was heated at 150° C. under microwave irradiation for 10 minutes. The mixture was diluted with ethyl acetate and extracted twice with water. The combined aqueous extracts were concentrated to give the title compound as a purple oil (240 mg, including residual TFA and/or water). 1H NMR (methanol-d4) 7.42 (1H, t), 7.07 (1H, d), 7.04 (1H, d), 4.64 (4H, br.s), 4.47-4.44 (2H, m), 3.65-3.63 (2H, m), 3.01 (6H, s). MS: [M+H]+ 207.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08101648B2 |
| Source dataset | uspto-grants-2012_01 |
| ORD ID | ord-95b11e5665164127ac11b760609bc65a |
| Source note | uspto-grants-2012_01 |