HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2209271Generated: October 30, 2026
tert-Butyl piperazine-1-carboxylate → Tert-butyl 4-(6-chloro-2-methoxypyridin-3-yl)piperazine-1-carboxylate
https://huagongshe.com/reaction/2209271
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | tert-Butyl piperazine-1-carboxylate | HCID 143452 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Reactant | 3-Bromo-6-chloro-2-methoxypyridine | HCID 53217454 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | Tert-butyl 4-(6-chloro-2-methoxypyridin-3-yl)piperazine-1-carboxylate | HCID 117843574 | — |
Reaction Steps
3-bromo-6-chloro-2-methoxypyridine (1.15 g, 5.17 mmol), tert-butyl piperazine-1-carboxylate (900 mg, 4.8 mmol), sodium tert-butoxide (1.39 g, 14.5 mmol), Pd2(dba)3 (130 mg, 0.15 mmol) and XantPhos (250 mg, 0.44 mmol) were taken up in toluene (36 mL) under Ar. The reaction mixture was heated to 70° C. and was stirred for 18 h. The mixture was cooled and partitioned between water and EtOAc. The phases were separated, and the organic phase was dried over Na2SO4, filtered, and concentrated. The crude residue was purified by silica gel chromatography (0-3% Et2O in DCM) to afford tert-butyl 4-(6-chloro-2-methoxypyridin-3-yl)piperazine-1-carboxylate 7.10. LCMS-ESI+ (m/z): [M+H]+ calcd for C15H23ClN3O3: 328.1; found: 328.3.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09376441B2 |
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| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-82a880b07aa64e04a1cb84a1c0414e8e |
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| Source note | uspto-grants-2016_06 |
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