Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Reactant | HCID 67538221 | HCID 67538221 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Catalyst | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Product | HCID 59396653 | HCID 59396653 | — |
Reaction Steps
7-bromo-1-cyclohexyl-3,4-dihydroisoquinoline (9.47 g) was dissolved in N-methyl-2-pyrrolidone (150 mL) to which tris(dibenzylideneacetone)dipalladium (2.97 g), 1,1′-bis(diphenylphosphino)ferrocene (7.19 g), and zinc cyanide (11.5 g) were then added, followed by stirring at 120° C. for 18 hours. Then, water was added to the reaction liquid which was then filtered through celite to separate the insoluble materials. The insoluble materials were extracted with EtOAc, washed with saturated brine, and then dried over magnesium sulfate. The solvent was evaporated and the resulting residue was purified by silica gel column chromatography (hexane-EtOAc) to obtain 1-cyclohexyl-3,4-dihydroisoquinoline-7-carbonitrile (7.19 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08263607B2 |
|---|
| Source dataset | uspto-grants-2012_09 |
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| ORD ID | ord-6943826c0d17435ba9c3f9b7b98b92c1 |
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| Source note | uspto-grants-2012_09 |
|---|
