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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1633616Generated: November 1, 2026

Water → Cyclopropyl-{6-[1-(4-fluoro-phenyl)-1h-indol-5-yloxy]-hexyl}-methyl-amine

https://huagongshe.com/reaction/1633616

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantDiethyl EtherHCID 3283—
ReactantDimethylformamideHCID 6228—
ReactantSodium hydrideHCID 24758—
Reactant5-(6-Bromo-hexyloxy)-1-(4-fluoro-phenyl)-1H-indoleHCID 11749612—
ProductCyclopropyl-{6-[1-(4-fluoro-phenyl)-1h-indol-5-yloxy]-hexyl}-methyl-amineHCID 1867944073%

Reaction Steps

195 mg (0.5 mmol) 5-(6-Bromo-hexyloxy)-1-(4-fluoro-phenyl)-1H-indole in 2.5 ml DMF were treated with 185 mg (1 mmol) cyclopropyl-methyl amine·CF3CO2H and 96 mg (2 mmol, 50% in mineral oil) NaH at RT for 2 h and at 60° C. for 3 h. At RT, ether and water were added and the inorganic phase was extracted with ether. The combined organic phases were washed with water, dried over Na2SO4 and evaporated. Purification on silica gel with hexane/ether 1:1 yielded 140 mg (73%) Cyclopropyl-{6-[1-(4-fluoro-phenyl)-1H-indol-5-yloxy]-hexyl}-methyl-amine as light yellow oil, MS: 381 (MH+).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06503907B2
Source datasetuspto-grants-2003_01
ORD IDord-938d48b6940f48ac8d2b9d98ce7707bd
Source noteuspto-grants-2003_01