Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | Thiophene | HCID 8030 | — |
| Reactant | Potassium Acetate | HCID 517044 | — |
| Reactant | HCID 18176645 | HCID 18176645 | — |
| Reactant | HCID 178418361 | HCID 178418361 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 18176648 | HCID 18176648 | 73% |
Reaction Steps
A mixture of intermediate 7 (0.03 mol) and paraformaldehyde (2 g) in methanol (150 ml) was hydrogenated with palladium on carbon (2 g) as a catalyst in the presence of thiophene (4%, 2 ml) and potassium acetate (4 g). After uptake of hydrogen gas (1 equivalent), the catalyst was filtered off and the filtrate was evaporated. The residue was stirred in water and this mixture was extracted with DCM. The separated organic layer was dried, filtered, and the solvent evaporated. The residue was dissolved in DIPE and converted into the hydrochloric acid salt (1:1) with HCl/2-propanol. The precipitate was filtered off and dried, yielding 8.22 g (73%) of N-methyl-N-[4-[3-(trifluoro-methyl)phenoxy]butyl]benzenemethanamine hydrochloride (intermediate 8).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06602873B2 |
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| Source dataset | uspto-grants-2003_08 |
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| ORD ID | ord-7291af5907aa4dabaa019d7d416784e5 |
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| Source note | uspto-grants-2003_08 |
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