Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | tert-Butyl piperazine-1-carboxylate | HCID 143452 | — |
| Reactant | HCID 70872667 | HCID 70872667 | — |
| Catalyst | Binap, (A+-)- | HCID 634876 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 86719547 | HCID 86719547 | 33.3% |
Reaction Steps
A solution of methyl 5-bromo-3-(cyclopentyl(methyl)amino)-2-methylbenzoate (1 g, 3.07 mmol), tert-butyl piperazine-1-carboxylate (0.85 g, 4.61 mmol) and Cs2CO3 (0.5 g, 1.53 mmol) in toluene (25 mL) was purged with argon for 10 min. Then, Pd2(dba)3 (0.31 g, 0.307 mmol) and BINAP (0.038 g, 0.061 mmol) was added to it and argon purged again for 10 min. The reaction mixture was stirred at 100° C. for 8 h. After completion, water was added to it and extracted with ethyl acetate. The combined organic layers were washed with water, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford crude material which was purified by column chromatography to afford the title compound (0.44 g, 33.3%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09376422B2 |
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| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-6938e1a9fc994ae697777b7ce62fe3e5 |
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| Source note | uspto-grants-2016_06 |
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