HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2404427Generated: November 1, 2026
Benzyl mercaptan → 2-[(3-benzylsulfanylphenyl)(1-methylpiperidin-4-yloxy)methyl]-1H-benzimidazole
https://huagongshe.com/reaction/2404427
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzyl mercaptan | HCID 7509 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | 2-[(3-bromophenyl)(1-methylpiperidin-4-yloxy)methyl]-1H-benzimidazole | HCID 56947989 | — |
| Catalyst | 1,5-Diphenylpenta-1,4-dien-3-one;palladium | HCID 154270 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 2-[(3-benzylsulfanylphenyl)(1-methylpiperidin-4-yloxy)methyl]-1H-benzimidazole | HCID 66835717 | — |
Reaction Steps
A screw-cap tube is charged with 2-[(3-bromophenyl)(1-methylpiperidin-4-yloxy)methyl]-1H-benzimidazole (200 mg), palladium bis(dibenzylideneacetone) (14 mg), Xantphos (14 mg), benzyl mercaptan (59 μL), Diisopropylethylamine (174 μL) and 1,4-dioxane (2 mL). The tube is evacuated, filled with argon and sealed. After stirring at 120° C. for 24 h, the mixture is diluted with ethyl acetate and water and the aqueous phase is extracted with ethyl acetate. The pooled organic extracts are dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by chromatography (gradient dichloromethane/methanol/ammonia from 100/0/0 to 95/5/0.5) to afford 2-[(3-benzylsulfanylphenyl)(1-methylpiperidin-4-yloxy)methyl]-1H-benzimidazole
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08802664B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-e7cc2326ad834f8aa6a756ddd01ce97e |
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| Source note | uspto-grants-2014_08 |
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