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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 843164Generated: October 31, 2026

N,N,N',N'-Tetramethylazodicarboxamide → HCID 53778444, compound

https://huagongshe.com/reaction/843164

Reaction equation

Participants

RoleNameHCIDCharge
ReactantN,N,N',N'-TetramethylazodicarboxamideHCID 4278—
ReactantTributylphosphineHCID 13831—
ReactantPiperidin-4-olHCID 79341—
ReactantEthyl 4-hydroxy-3-methyl-1-benzofuran-2-carboxylateHCID 748649—
SolventBenzeneHCID 241—
SolventEthyl AcetateHCID 8857—
ProductHCID 53778444HCID 5377844417.4%

Reaction Conditions

Temperature60 °C

Reaction Steps

A mixture of 4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester (100 mg), 4-hydroxypiperidine (46 mg), tributylphosphine (170 μl) and 1,1′-azobis(N,N-dimethylformamide) (120 mg) in benzene (2 ml) was heated at 60° C. for one hour. The suspension was diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate and evaporated to dryness. The residue was separated by silica gel column chromatography developed by dichloromethane-methanol to give 3-methyl-4-(piperidin-4-yloxy)-benzofuran-2-carboxylic acid ethyl ester (24 mg) as a colorless oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06376491B1
Source datasetuspto-grants-2002_04
ORD IDord-030024d306624439a7a142e45cfe9ce1
Source noteuspto-grants-2002_04