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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 420569Generated: October 30, 2026

Diethyl Ether → 2-[4-(5-Bromothiazole-2-yl)-2,6-dimethyl piperazine-1-yl]ethanol

https://huagongshe.com/reaction/420569

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiethyl EtherHCID 3283—
ReactantAmmonium ChlorideHCID 25517—
ReactantDiisobutylaluminumhydrideHCID 21225700—
Reactant[4-(5-Bromothiazole-2-yl)-2,6-dimethyl piperazine-1-yl]acetic acid methyl esterHCID 66657554—
SolventTetrahydrofuranHCID 8028—
Product2-[4-(5-Bromothiazole-2-yl)-2,6-dimethyl piperazine-1-yl]ethanolHCID 6665780671.4%

Reaction Conditions

Temperature-78 °C

Reaction Steps

To a solution of [4-(5-bromothiazole-2-yl)-2,6-dimethyl piperazine-1-yl]acetic acid methyl ester (20.1 g) in tetrahydrofuran (300 mL) was added dropwise diisobutyl aluminium hydride (1M toluene solution, 200 mL) at −78° C. The mixture was stirred at −78° C. for 3.5 hours. To the reaction solution were added aqueous ammonium chloride solution (150 mL) and diethyl ether (45 mL). The insoluble material was filtrated. The filtrate was extracted diethyl ether. The organic layer was washed with water and brine, and dried over magnesium sulphate. The solvent was evaporated under reduced pressure. The residue was purified by column chromatograph on silica gel to give the title compound (13.2 g). Yield: 71%.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08097610B2
Source datasetuspto-grants-2012_01
ORD IDord-c6b3a8193c2a4cd99cdb65a047a1fc37
Source noteuspto-grants-2012_01