Sodium Iodide → N-[4-diethylamino-1,1-dimethyl-2-butynyl]-4,4-diphenyl-2-cyclopentenylamine
Reaction equation
[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][CH:10](Cl)[CH:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:19]([N:21]([CH2:29][CH3:30])[CH2:22][C:23]#[C:24][C:25]([NH2:28])([CH3:27])[CH3:26])[CH3:20].[I-].[Na+]>CC(C)=O>[CH2:29]([N:21]([CH2:19][CH3:20])[CH2:22][C:23]#[C:24][C:25]([NH:28][CH:10]1[CH2:11][C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:8]=[CH:9]1)([CH3:26])[CH3:27])[CH3:30]Participants
Procedure
A mixture of 4,4-diphenyl-2-cyclopentenyl chloride (0.60 g), 4-diethylamino-1,1-dimethyl-2-butynylamine (0.79 g) and a catalytic amount of sodium iodide in acetone (5 ml) was refluxed for 8 hours. After being cooled, the solvent was removed off under reduced pressure and the residue was purified with column chromatography on silica gel with a mixture of chloroform and methanol as an eluent to give N-[4-diethylamino-1,1-dimethyl-2-butynyl]-4,4-diphenyl-2-cyclopentenylamine (0.54 g). The free amine obtained above was dissolved in chloroform, and to the solution was added hydrogen chloride in methanol (0.18 g/ml, 1 ml). The solution was evaporated in vacuo and triturated with a mixture of ethanol and isopropyl alcohol to give its hydrochloride (0.45 g).
Workup
- temperatureAfter being cooled
- customthe solvent was removed off under reduced pressure
- customthe residue was purified with column chromatography on silica gel with a mixture of chloroform and methanol as an eluent
Sources & evidence
- ORD record
- ord-9ba77c91ab904f1590191cd4b543f3ac
- Source dataset
- uspto-grants-1993_10
- Patent number
- US05256824
Reaction notes
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