Sodium Iodide → N-t-butyl-4,4-diphenyl-2-cyclopentenylamine

HRID 1657284Notes

Reaction equation

HRID 1657284 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.[C:19]([NH2:23])([CH3:22])([CH3:21])[CH3:20].[I-].[Na+]>CC(C)=O>[C:19]([NH:23][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)([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6385Tert-ButylamineHCID 107534844,4-Diphenyl-2-cyclopentenyl chloride

Product 1

HCID 9796063N-t-butyl-4,4-diphenyl-2-cyclopentenylamine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4,4-diphenyl-2-cyclopentenyl chloride (0.20 g), t-butylamine (2 ml) and a catalytic amount of sodium iodide in acetone (4 ml) was refluxed for 15 hours and cooled. The mixture was evaporated in vacuo and water was added thereto extracted with ethyl acetate. The extract was washed with brine, dried over sodium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of chloroform and methanol as an eluent to give N-t-butyl-4,4-diphenyl-2-cyclopentenylamine (0.15 g).

Workup

  1. temperaturecooled
  2. customThe mixture was evaporated in vacuo and water
  3. additionwas added
  4. extractionthereto extracted with ethyl acetate
  5. washThe extract was washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by column chromatography on silica gel with a mixture of chloroform and methanol as an eluent

Sources & evidence

ORD record
ord-951ffa7422d34cf39caf86b2fc35c34a
Source dataset
uspto-grants-1993_10
Patent number
US05256824

Reaction notes

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