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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2188642Generated: October 29, 2026

Morpholine → 8-Benzyl-3-(morpholin-4-yl)-6,7,8,9-tetrahydropyrazino[2,3-f][1,4]oxazepine

https://huagongshe.com/reaction/2188642

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMorpholineHCID 8083—
Reactant2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 11155794—
ReactantSodium t-butoxideHCID 23676156—
Reactant8-Benzyl-3-chloro-6,7,8,9-tetrahydropyrazino[2,3-f][1,4]oxazepineHCID 86648981—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
SolventWaterHCID 962—
SolventTolueneHCID 1140—
Product8-Benzyl-3-(morpholin-4-yl)-6,7,8,9-tetrahydropyrazino[2,3-f][1,4]oxazepineHCID 6699313168%

Reaction Conditions

Temperature100 °C

Reaction Steps

A suspension of 8-benzyl-3-chloro-6,7,8,9-tetrahydropyrazino[2,3-f][1,4]oxazepine (322 mg), morpholine (0.13 mL), Pd2(dba)3 (22 mg), XPhos (45 mg) and sodium tert-butoxide (282 mg) in toluene (10 mL) was stirred under an argon atmosphere at 100° C. for 3 hr. Water was added to the reaction mixture, the aqueous layer was extracted with ethyl acetate, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient: 16→100% ethyl acetate/hexane) to give the title compound (259 mg, 68%) as a colorless oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08324201B2
Source datasetuspto-grants-2012_12
ORD IDord-97f1b6f97beb478889574f4b18259bb9
Source noteuspto-grants-2012_12