Hydrochloric Acid → 1-(2-Diethylaminoethyl)-2-phenyl-5-methyl-4,5,6,7-tetrahydroindole hydrochloride
Reaction equation
[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][NH2:6])[CH3:2].[CH3:9][CH:10]1[CH2:15][CH2:14][C:13](=O)[CH:12]([CH2:17][C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=O)[CH2:11]1.O.[ClH:27]>C(O)(=O)C.CCOCC>[ClH:27].[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][N:6]1[C:13]2[CH2:14][CH2:15][CH:10]([CH3:9])[CH2:11][C:12]=2[CH:17]=[C:18]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:2]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 5.94 g (0.05 mole) of 2-diethylaminoethylamine and 11.52 g (0.05 mole) of 4-methyl-2-phenacyl-cyclohexanone in glacial acetic acid is refluxed under nitrogen for 8 hours. Water is added to the mixture, and the mixture is acidified with dilute hydrochloric acid and washed with ether. The aqueous solution is basified with 10% sodium carbonate and extracted with ether to give a light brown oil. The oil is dissolved in ether and ethereal hydrogen chloride is added to give a granular off-white salt. The salt is recrystallized from an isopropanol-ether mixture and then from a methanol-ether pair to give 1-(2-diethylaminoethyl)-2-phenyl-5-methyl-4,5,6,7-tetrahydroindole hydrochloride as light tan crystals, m.p. 171°-177° C.
Workup
- washwashed with ether
- extractionextracted with ether
- customto give a light brown oil
- customto give a granular off-white salt
- customThe salt is recrystallized from an isopropanol-ether mixture
Sources & evidence
- ORD record
- ord-813a829f721a45cfab7946cdd045729a
- Source dataset
- uspto-grants-1976_12
- Patent number
- US03997557
Reaction notes
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