Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cyclohexanone | HCID 7967 | — |
| Reactant | 2-Amino-1-cyclopentene-1-carbonitrile | HCID 287275 | — |
| Reactant | Ipidacrine hydrochloride hydrate | HCID 6917941 | — |
| Solvent | Benzene | HCID 241 | — |
| Product | Hydrochloric Acid | HCID 313 | — |
| Product | Ipidacrine | HCID 604519 | — |
Reaction Steps
As a synthetic process for ipidacrine hydrochloride hydrate, 2-amino-1-cyclopentene-1-carbonitrile (or 1-amino-2-cyanocyclopentene-1) and cyclohexanone are first heated under reflux with polyphosphoric acid in dry benzene to obtain ipidacrine (i.e., 9-amino-2,3,5,6,7,8-hexahydro-lH-cyclopenta[b]quinoline) and hydrogen chloride gas is then passed through the ethanol solution of the resultant reaction mixture to yield ipidacrine hydrochloride hydrate (i.e., 9-amino-2,3,5,6,7,8-hexahydro-1H-cyclopenta [b]quinoline-hydrochloride hydrate) has been reported (for example, see JP-B (Kokoku)-63-35611). Further, it is described that ipidacrine is obtained even if reacting 5,5-pentamethylen-7-oxo-1,2,3,4,6,7-hexahydrocyclopenta [d]pyrimidine obtained as a byproduct in the above reaction with phosphorus oxychloride in toluene (for example, see JP-B (Kokoku)-3-54922).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06433173B1 |
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| Source dataset | uspto-grants-2002_08 |
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| ORD ID | ord-dfd8f78def7c4d088964b12157eb9a76 |
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| Source note | uspto-grants-2002_08 |
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