Sodium Iodide → HCID 19787490, compound

HRID 1657283Notes

Reaction equation

HRID 1657283 reaction equation
[CH:1]1([C:4]2([CH:10]3[CH2:12][CH2:11]3)[CH2:8][CH:7](O)[CH:6]=[CH:5]2)[CH2:3][CH2:2]1.CS([Cl:17])(=O)=O.[I-].[Na+].[C:20]([NH2:24])([CH3:23])([CH3:22])[CH3:21]>CC(C)=O.C(N(CC)CC)C>[ClH:17].[C:20]([NH:24][CH:7]1[CH2:8][C:4]([CH:10]2[CH2:12][CH2:11]2)([CH:1]2[CH2:3][CH2:2]2)[CH:5]=[CH:6]1)([CH3:23])([CH3:22])[CH3:21]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6385Tert-ButylamineHCID 31297Methanesulfonyl chlorideHCID 19787467HCID 19787467, compound

Product 1

HCID 19787490HCID 19787490, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 4,4-dicyclopropyl-2-cyclopenten-1-ol (0.52 g) in acetone (5 ml) were added methanesulfonyl chloride (0.27 ml) and triethylamine (0.49 ml) with ice bath cooling. After being stirred for 10 minutes, sodium iodide (0.52 g) was added thereto, and the mixture was stirred for 10 minutes. To the mixture was added t-butylamine (6.4 ml), and the mixture was stirred at room temperature overnight. The solvent was evaporated in vacuo, and then cold water was added thereto, 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, and hydrogen chloride in ethanol (8.9N, 0.5 ml) was added thereto, and evaporated in vacuo. The residue was crystallized from diethyl ether to give N-t-butyl-4,4-dicyclopropyl-2-cyclopentenylamine hydrochloride (0.51 g). These crystals were recrystallized from a mixture of isopropyl alcohol and ethyl acetate to give pure one (0.41 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 10 minutes
  3. stirringthe mixture was stirred at room temperature overnight
  4. customThe solvent was evaporated in vacuo
  5. additioncold water was added
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe extract was washed with brine
  8. dry with materialdried over sodium sulfate
  9. customevaporated in vacuo
  10. dissolutionThe residue was dissolved in ethyl acetate
  11. additionhydrogen chloride in ethanol (8.9N, 0.5 ml) was added
  12. customevaporated in vacuo
  13. customThe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-ab70704abf454378945f0beea16dccc0
Source dataset
uspto-grants-1993_10
Patent number
US05256824

Reaction notes

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