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Sodium Iodide → N-[4-diethylamino-1,1-dimethyl-2-butynyl]-4,4-diphenyl-2-cyclopentenylamine

HRID 1657287
Notes
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Reaction equation

HRID 1657287 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 107534844,4-Diphenyl-2-cyclopentenyl chlorideHCID 538468214-Diethylamino-1,1-dimethyl-2-butynylamine

Product 1

HCID 19787466N-[4-diethylamino-1,1-dimethyl-2-butynyl]-4,4-diphenyl-2-cyclopentenylamineYield 59.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

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

  1. temperatureAfter being cooled
  2. customthe solvent was removed off under reduced pressure
  3. 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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05256824

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes