HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → tert-Butyl 4-(5-bromo-3-methylpyridin-2-yl)piperazine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | tert-Butyl piperazine-1-carboxylate | HCID 143452 | — |
| Reactant | 2,5-Dibromo-3-methylpyridine | HCID 817680 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | tert-Butyl 4-(5-bromo-3-methylpyridin-2-yl)piperazine-1-carboxylate | HCID 46739269 | — |
Reaction Steps
Heat a solution of 2,5-dibromo-3-methyl-pyridine (Chontech Inc.) (12.6 g, 50.3 mmol), piperazine-1-carboxylic acid tert-butyl ester (11.7 g, 62.9 mmol) and DIEA (13.3 g, 102.0 mmol) in DMA at 130° C. for 36 h. Partition the dark brown reaction mixture between water and EtOAc. Wash the EtOAc layer with water (1×) and brine (1×), dry (Na2SO4) and concentrate under reduced pressure to give the crude product. Purify by flash chromatography, eluting with 9:1 hexanes:EtOAc, increasing to 3:1 hexanes:EtOAc to provide the title compound as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08334382B2 |
| Source dataset | uspto-grants-2012_12 |
| ORD ID | ord-0172bdeeda314b9d9a7865bc2ace6fa7 |
| Source note | uspto-grants-2012_12 |