HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dimethoxyethane → 1-[6-(N-Pyrrolidinyl)-3-pyridyl]-4-tert-butoxycarbonyl homopiperazine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dimethoxyethane | HCID 8071 | — |
| Reactant | Pyrrolidine | HCID 31268 | — |
| Reactant | Tert-butyl 4-(6-bromopyridin-3-yl)-1,4-diazepane-1-carboxylate | HCID 22478562 | — |
| Reactant | Potassium tert-butoxide | HCID 23665647 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Product | 1-[6-(N-Pyrrolidinyl)-3-pyridyl]-4-tert-butoxycarbonyl homopiperazine | HCID 22478457 | — |
Reaction Steps
A stirred solution of 1-(6-Bromo-3-pyridyl)-4-tert-butoxycarbonyl homopiperazine (0.71 g, 2.0 mmol), pyrrolidine (2.0 g, 20 mmol), potassium tert-butoxide (0.45 g, 4.0 mmol), tetrakis(triphenylphosphine)palladium(0) (0.12 g, 0.10 mmol) and 1.2-dimethoxyethane was stirred at reflux overnight. Water (40 ml) was added and the mixture was extracted twice with ethyl acetate (20 ml) Chromatography on silica gel with a mixture of petroleum:ethyl acetate (1:1) gave the title compound as free base. Yield 0.21 g, 30%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06825189B1 |
| Source dataset | uspto-grants-2004_11 |
| ORD ID | ord-b5a31fe1fe64452eaaab5d34b512771f |
| Source note | uspto-grants-2004_11 |