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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 886897Generated: October 31, 2026

1,4-Dioxane → HCID 68578580, compound

https://huagongshe.com/reaction/886897

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,4-DioxaneHCID 31275—
Reactant2,6-Dimethylmorpholine, cis-HCID 641500—
ReactantSodium t-butoxideHCID 23676156—
ReactantHCID 68578192HCID 68578192—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
Catalyst2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 11155794—
SolventWaterHCID 962—
ProductHCID 68578580HCID 68578580135.9%

Reaction Steps

A solution of tert-butyl 8-bromo-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (300 mg, 0.609 mmol), cis-2,6-dimethylmorpholine (0.370 ml, 3.00 mmol), X-phos (26.1 mg, 0.0548 mmol), tris(dibenzylideneacetone)dipalladium(0) (16.6 mg, 0.0181 mmol), sodium tert-butoxide (131 mg, 1.37 mmol) and dioxane (6 ml) was stirred under an argon atmosphere for 2 hr at 80° C. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give the desired product (300 mg, 90.4%) as an oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08247403B2
Source datasetuspto-grants-2012_08
ORD IDord-c1e08a59f79146abb54cf93de9e8ee45
Source noteuspto-grants-2012_08