HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → 4,4'-(1-(4-Tert-butylphenyl)pyrrolidine-2,5-diyl)dibenzonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Ammonium Hydroxide | HCID 14923 | — |
| Reactant | 2,5-Bis(4-bromophenyl)-1-(4-tert-butylphenyl)pyrrolidine | HCID 58226837 | — |
| Reactant | HCID 178418546 | HCID 178418546 | — |
| Solvent | Water | HCID 962 | — |
| Product | 4,4'-(1-(4-Tert-butylphenyl)pyrrolidine-2,5-diyl)dibenzonitrile | HCID 67236494 | 78% |
Reaction Steps
A solution of Example 42C (2.0 g, 3.9 mmol) and copper(I) cyanide (1.047 g, 11.69 mmol) in DMF (19 mL) was heated in a microwave for 7 hours at 160° C. Afterwards the mixture was poured in water (700 mL) and then concentrated ammonium hydroxide (40 mL) was added and the solution extracted with EtOAc. The organic extract was dried, filtered, concentrated and the residue purified by flash chromatography (silica gel, EtOAc/hexanes) to afford 1.23 g (78%) of the title compound. MS (ESI) m/z 406 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09006387B2 |
| Source dataset | uspto-grants-2015_04 |
| ORD ID | ord-900f966cda17430b9a399a9099ce2e8c |
| Source note | uspto-grants-2015_04 |