HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → (S)-2-(3-(((3,4-Dimethoxybicyclo[4.2.0]octa-1(6),2,4-trien-7-yl)methyl)(methyl)amino)propyl)isoindoline-1,3-dione
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | N-3-Bromopropylphthalimide | HCID 21611 | — |
| Reactant | (S)-1-(3,4-Dimethoxybicyclo(4.2.0)octa-1,3,5-trien-7-yl)-N-methylmethanamine | HCID 11499437 | — |
| Solvent | Acetone | HCID 180 | — |
| Product | (S)-2-(3-(((3,4-Dimethoxybicyclo[4.2.0]octa-1(6),2,4-trien-7-yl)methyl)(methyl)amino)propyl)isoindoline-1,3-dione | HCID 68163162 | 97% |
Reaction Steps
5.3 g (25.5 mmoles) of 1-[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-N-methyl-methanamine and 6.8 g (25.5 mmoles) of 2-(3-bromopropyl)-1H-isoindole-1,3(2H)-dione are dissolved in 230 mL of acetone. 13 g (95 mmoles, 3.7 eq.) of potassium carbonate are added to the resulting solution. The mixture is then heated at reflux for 24 hours. After returning to ambient temperature, the potassium carbonate is filtered off and the filtrate is evaporated to dryness. The residue is taken up in water and extracted with dichloromethane. The organic phase is dried over MgSO4, filtered and evaporated to dryness. 9.7 g of expected product are obtained in the form of a pale yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08476426B2 |
| Source dataset | uspto-grants-2013_07 |
| ORD ID | ord-161b53f531d3469ba20d5b7b1a8fc47e |
| Source note | uspto-grants-2013_07 |