Cyclohexanone → Hydrochloric Acid
Reaction equation
[CH2:1]1[CH2:6][C:5]2[C:7]([NH2:14])=[C:8]3[C:12](=[N:13][C:4]=2[CH2:3][CH2:2]1)[CH2:11][CH2:10][CH2:9]3.O.[ClH:16].NC1CCCC=1C#N.C1(=O)CCCCC1>C1C=CC=CC=1>[CH2:1]1[CH2:6][C:5]2=[C:7]([NH2:14])[C:8]3[CH2:9][CH2:10][CH2:11][C:12]=3[N:13]=[C:4]2[CH2:3][CH2:2]1.[ClH:16]Participants
Reactant 3
Product 2
Reagents, catalysts & solvents 1
Procedure
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).
Sources & evidence
- ORD record
- ord-dfd8f78def7c4d088964b12157eb9a76
- Source dataset
- uspto-grants-2002_08
- Patent number
- US06433173B1
Reaction notes
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