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

HRID 1657285Notes

Reaction equation

HRID 1657285 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:12])[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+].C1OCCOCCOCCOCCOCCOC1>C(Cl)Cl>[ClH:12].[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

6

Reactant 4

HCID 5238Sodium IodideHCID 6385Tert-ButylamineHCID 2855718-Crown-6HCID 107534844,4-Diphenyl-2-cyclopentenyl chloride

Product 1

HCID 19787440N-t-butyl-4,4-diphenyl-2-cyclopentenylamine hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4,4-diphenyl-2-cyclopentenyl chloride (0.30 g), t-butylamine (1.24 ml), a catalytic amount of sodium iodide and 18-crown-6 in methylene chloride (3 ml) was refluxed for 47 hours and cooled. The solvent was removed off in vacuo, and water was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed with brine, dried over sodium sulfate and evaporated under reduced pressure. To the residue were added ethyl acetate (5 ml) and 3N hydrochloric acid (2 ml) with cooling in an ice bath, and the mixture was stirred for 3 hours. The precipitate was collected by filtration, washed with ethyl acetate, water, ethyl acetate successively and dried to give N-t-butyl-4,4-diphenyl-2-cyclopentenylamine hydrochloride (0.28 g).

Workup

  1. temperaturecooled
  2. customThe solvent was removed off in vacuo, and water
  3. additionwas added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated under reduced pressure
  8. additionTo the residue were added ethyl acetate (5 ml) and 3N hydrochloric acid (2 ml)
  9. temperaturewith cooling in an ice bath
  10. filtrationThe precipitate was collected by filtration
  11. washwashed with ethyl acetate, water, ethyl acetate successively
  12. customdried

Sources & evidence

ORD record
ord-1b8ea590429a401c934c1dbbe12b6d84
Source dataset
uspto-grants-1993_10
Patent number
US05256824

Reaction notes

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