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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1183336Generated: October 26, 2026

Acetic Acid → (1-Benzyl-piperidin-4-yl)-[5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]-amine

https://huagongshe.com/reaction/1183336

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AcidHCID 176—
Reactant1-Benzyl-4-piperidoneHCID 19220—
ReactantSodium cyanoborohydrideHCID 5003444—
Reactant5-(4-Bromophenyl)-3-methylisoxazol-4-amineHCID 58218537—
SolventMethanolHCID 887—
Product(1-Benzyl-piperidin-4-yl)-[5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]-amineHCID 66577607—

Reaction Conditions

Temperature0 °C

Reaction Steps

5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-ylamine (0.500 g, 1.73 mmol) and 1-benzyl-piperidin-4-one were mixed with acetic acid (0.200 mL) in MeOH (8 mL). The reaction was cooled to 0° C. and stirred for one hour before sodium cyanoborohydride (0.108 g, 1.74 mmol) was added. The reaction was allowed to warm to room temperature and was monitored by analytical LCMS. When complete, the reaction was quenched with aqueous sodium bicarbonate then submitted to standard workup procedures. The crude material was purified by silica gel chromatography (0-100% EtOAc in hexanes) to afford the title compound

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08664220B2
Source datasetuspto-grants-2014_03
ORD IDord-ff112993a7724bc692c3532bd186a8e0
Source noteuspto-grants-2014_03