Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Thiophene | HCID 8030 | — |
| Reactant | HCID 12891532 | HCID 12891532 | — |
| Reactant | HCID 178418361 | HCID 178418361 | — |
| Catalyst | Platinum | HCID 23939 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 12891722 | HCID 12891722 | 42% |
Reaction Steps
To 1 part of a solution of 2 parts of thiophene in 40 parts of ethanol are added 3.3 parts of 1-(4-fluorophenylmethyl)-N-{1-[2-(4-nitrophenyl)ethyl]-4-piperidinyl}-1H-benzimidazol-2-amine and 120 parts of methanol. The whole is hydrogenated at normal pressure and at room temperature with 2 parts of platinum-on-charcoal catalyst 5%. After the calculated amount of hydrogen is taken up, the catalyst is filtered off and the filtrate is evaporated. The residue is purified by column-chromatography over silica gel using a mixture of methylbenzene and methanol (95:5 by volume) saturated with ammonia, as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from 2-propanol, yielding 1.3 parts (42%) of N-{1-[2-(4-aminophenyl)ethyl]-4-piperidinyl}-1-(4-fluorophenylmethyl)-1H-benzimidazol-2-amine; mp. 195.4° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04219559 |
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| Source dataset | uspto-grants-1980_08 |
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| ORD ID | ord-0434d351c44543548595f1b305260dff |
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| Source note | uspto-grants-1980_08 |
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