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

HRID 1657282Notes

Reaction equation

HRID 1657282 reaction equation
[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:11](O)[CH:10]=[CH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CS([Cl:23])(=O)=O.[I-].[Na+].[C:26]([NH2:30])([CH3:29])([CH3:28])[CH3:27]>CC(C)=O.O.C(N(CC)CC)C>[ClH:23].[C:26]([NH:30][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)([CH3:29])([CH3:28])[CH3:27]

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 6385Tert-ButylamineHCID 31297Methanesulfonyl chlorideHCID 100371165,5-Diphenyl-2-cyclopenten-1-ol

Product 1

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

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 5,5-diphenyl-2-cyclopenten-1-ol (0.30 g) in acetone were added methanesulfonyl chloride (0.12 ml) and triethylamine (0.21 ml) at 1° C. to 3° C. After being stirred for 15 minutes sodium iodide (0.23 g) was added thereto and the mixture was stirred for 10 minutes. To the mixture was added t-butylamine (2.67 ml) at -1° C. to 2° C. and the mixture was stirred at room temperature overnight. Cold water was added to the mixture and the mixture was extracted with ethyl acetate. The extract was washed with brine, dried over sodium sulfate and evaporated in vacuo. The residue was dissolved in ethyl acetate. To the solution was added 3N hydrochloric acid (1 ml) with cooling in an ice bath, and the mixture was stirred for 30 minutes. The resulting precipitates were collected by filtration, washed with water, ethyl acetate successively and dried to give N-t-butyl-4,4-diphenyl-2-cyclopentenylamine hydrochloride (0.31 g).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at room temperature overnight
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo
  7. dissolutionThe residue was dissolved in ethyl acetate
  8. additionTo the solution was added 3N hydrochloric acid (1 ml)
  9. temperaturewith cooling in an ice bath
  10. stirringthe mixture was stirred for 30 minutes
  11. customThe resulting precipitates
  12. filtrationwere collected by filtration
  13. washwashed with water, ethyl acetate successively
  14. customdried

Sources & evidence

ORD record
ord-fa080201e4fc4734978ba59a17926e99
Source dataset
uspto-grants-1993_10
Patent number
US05256824

Reaction notes

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