HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dichloromethane → 5-(4-Methyl-piperazin-1-ylmethyl)-1,3-dihydro-isoindole-2-carboxylic acid benzyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | 1-Methylpiperazine | HCID 53167 | — |
| Reactant | 5-Methanesulfonyloxymethyl-1,3-dihydro-isoindole-2-carboxylic acid benzyl ester | HCID 57990212 | — |
| Solvent | Water | HCID 962 | — |
| Product | 5-(4-Methyl-piperazin-1-ylmethyl)-1,3-dihydro-isoindole-2-carboxylic acid benzyl ester | HCID 57990208 | 47% |
Reaction Steps
DCM (33 L) and N-methylpiperazine (21.45 L, 193.4 mol) were stirred at 25° C. and the solution from step 8 added over a minimum of 30 mins such that temperature 20-30° C. After stirring the solution for a further 30 mins water (55 L) was added and the organic phase was washed with water (2×55 L). The product was extracted into 0.8M HCl (66 L) and the layers separated. The aqueous phase was washed with DCM (55 L) and then basified with 2M NaOH to pH 10-11 and the product was extracted into EtOAc (2×55 L). The combined organic phase were filtered to remove solids and the evaporated followed by azeotroping with toluene and drying to constant weight to give the title compound, 6.63 kg (47% yield, 98% pure by hplc).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08883790B2 |
| Source dataset | uspto-grants-2014_11 |
| ORD ID | ord-750f534f13a94a89841514450055844a |
| Source note | uspto-grants-2014_11 |