HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethylenediamine → HCID 68576326, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethylenediamine | HCID 3301 | — |
| Reactant | 4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbonitrile | HCID 59837394 | — |
| Catalyst | Cupric acetate | HCID 8895 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | Ammonia methanol | HCID 21705897 | — |
| Product | HCID 68576326 | HCID 68576326 | 31% |
Reaction Steps
4-[4-(3-Pyrrolidin-1-yl-propoxy)-phenyl]-tetrahydro-pyran-4-carbonitrile (0.5 g, 3.1 mmol), ethylenediamine (1.5 mL, 22 mmol), copper (II) acetate (0.07 g, 0.3 mmol) and N-methylpyrrolidinone (1.5 mL) were combined and subjected to microwave (Smith Personal Synthesiser) irradiation at 220° C. for 1 hour. The reaction mixture was concentrated in vacuo to provide a brown oil. This was columned by flash chromatography on silica gel eluting with dichlromethane:methanol:ammonia (94:6:0.6 to 85:15:1.5) to provide the title compound (0.157 g, 31%) as a yellow oil. LRMS ESI+ m/z 358 [MH]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07456164B2 |
| Source dataset | uspto-grants-2008_11 |
| ORD ID | ord-c0e9231fcdaa4491873d8572353c975f |
| Source note | uspto-grants-2008_11 |