Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | tert-Butyl carbamate | HCID 77922 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | 4-(4-Bromophenyl)piperidine-4-carbonitrile | HCID 65814378 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 118114536 | HCID 118114536 | 39% |
Reaction Steps
The mixture of 4-(4-bromophenyl)piperidine-4-carbonitrile (347, 520 mg, 1.96 mmol), tert-butyl carbamate (460 mg, 3.92 mmol), Pd2(dba)3 (180 mg, 0.20 mmol), XantPhos (350 mg, 0.60 mmol), fine-powder Cs2CO3 (1.96 g, 6.0 mmol) in 30 mL dioxane was degassed using N2 stream for 5 min and stirred in 115° C. bath in N2 atmosphere for overnight. It was cooled to RT, diluted with EtOAc 200 mL and filtered. The filtrate was concentrated in vacuo and subjected to silica flash column using 0 to 30% MeOH in DCM to afford tert-butyl 4-(4-cyanopiperidin-4-yl)phenylcarbamate (348, 230 mg, 39%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09382246B2 |
|---|
| Source dataset | uspto-grants-2016_07 |
|---|
| ORD ID | ord-0a913e8f101340d6bdc6ad81549d2a00 |
|---|
| Source note | uspto-grants-2016_07 |
|---|
