HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1950131Generated: November 3, 2026
Ammonium Chloride → [5-Methoxy-2-(6-methoxynaphthalen-2-yl)phenyl][4-(2-piperidin-1-ylethoxy)phenyl]amine
https://huagongshe.com/reaction/1950131
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | 1-[2-(4-Bromophenoxy)ethyl]piperidine | HCID 867195 | — |
| Reactant | 5-Methoxy-2-(6-methoxynaphthalen-2-yl)phenylamine | HCID 23087511 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Catalyst | Tris(1,1-dimethylethyl)phosphine | HCID 83681 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | [5-Methoxy-2-(6-methoxynaphthalen-2-yl)phenyl][4-(2-piperidin-1-ylethoxy)phenyl]amine | HCID 57934396 | 97.8% |
Reaction Steps
A suspension of 5-methoxy-2-(6-methoxynaphthalen-2-yl)phenylamine (250 mg), 1-[2-(4-bromophenoxy)ethyl]piperidine (250 mg), tris(dibenzylideneacetone)dipalladium(0) (46 mg), tri-tert-butylphosphine (14 mg) and sodium tert-butoxide (130 mg) in toluene (2 ml) was stirred for 2.5 hours under nitrogen atmosphere at 100° C. A saturated aqueous solution of ammonium chloride was added thereto, extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by NH silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (415 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08399520B2 |
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| Source dataset | uspto-grants-2013_03 |
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| ORD ID | ord-9ec485a69e264683bf4301ecb1a641bb |
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| Source note | uspto-grants-2013_03 |
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