Triphenylphosphine → N-isopropyl-4,4-diphenyl-2-cyclopentenylamine

HRID 1657286Notes

Reaction equation

HRID 1657286 reaction equation
[C:1]1([C:7]2([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:11][CH:10]([N:12]=[N+]=[N-])[CH:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:21]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:26]=CC=C[CH:22]=1>CC(C)=O>[CH:21]([NH:12][CH:10]1[CH2:11][C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:8]=[CH:9]1)([CH3:26])[CH3:22]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 103552994,4-Diphenyl-2-cyclopentenyl azide

Product 1

HCID 10731252N-isopropyl-4,4-diphenyl-2-cyclopentenylamineYield 81.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4,4-diphenyl-2-cyclopentenyl azide (0.30 g) in acetone (3 ml) was added triphenylphosphine (0.33 g) at room temperature and refluxed for 21 hours. After being cooled, the solvent was removed under reduced pressure and a solution of sodium borohydride (0.22 g), in methanol (3 ml) was added thereto. After being stirred for 20 minutes, brine and ethyl acetate were added. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash column chromatography on silica gel with a mixture of chloroform and methanol as an eluent to give N-isopropyl-4,4-diphenyl-2-cyclopentenylamine (0.26 g).

Workup

  1. temperaturerefluxed for 21 hours
  2. temperatureAfter being cooled
  3. customthe solvent was removed under reduced pressure
  4. additiona solution of sodium borohydride (0.22 g), in methanol (3 ml) was added
  5. additionbrine and ethyl acetate were added
  6. customThe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried over magnesium sulfate
  9. customevaporated in vacuo
  10. customThe residue was purified by flash column chromatography on silica gel with a mixture of chloroform and methanol as an eluent

Sources & evidence

ORD record
ord-298db7198e764f99b39f09c32db19e79
Source dataset
uspto-grants-1993_10
Patent number
US05256824

Reaction notes

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