Iodoethane → 1-{[1-(4-Chlorophenyl)cyclopropyl]methyl}-1-ethylpyrrolidin-1-ium iodide

HRID 1743530Notes

Reaction equation

HRID 1743530 reaction equation
[CH2:1]([I:3])[CH3:2].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2([CH2:14][N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1>CO>[I-:3].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2([CH2:14][N+:15]3([CH2:1][CH3:2])[CH2:19][CH2:18][CH2:17][CH2:16]3)[CH2:12][CH2:13]2)=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 6340Iodoethane3×HCID 210157491-[1-(4-Chloro-phenyl)-cyclopropylmethyl]-pyrrolidine

Product 1

HCID 695836481-{[1-(4-Chlorophenyl)cyclopropyl]methyl}-1-ethylpyrrolidin-1-ium iodideYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-[1-(4-chloro-phenyl)-cyclopropylmethyl]-1-ethyl-pyrrolidinium iodide is prepared from the reaction of the parent amine 1-[1-(4-chloro-phenyl)-cyclopropylmethyl]-pyrrolidine with ethyl iodide. A 100 gm (0.42 mole) of the amine, 1-[1-(4-chloro-phenyl)-cyclopropylmethyl]-pyrrolidine, is dissolved in 1000 ml anhydrous methanol in a 3-liter 3-necked reaction flask (equipped with a mechanical stirrer and a reflux condenser). To this solution, 98 gm (0.62 mole) of ethyl iodide is added, and the mixture is stirred at room temperature for 72 hours. Then, 39 gm (0.25 mol.) of ethyl iodide is added and the mixture is heated at reflux for 3 hours. The reaction mixture is cooled down and excess ethyl iodide and the solvent are removed at reduced pressure on a rotary evaporator. The obtained dark tan-colored solids (162 gm) are further purified by dissolving in acetone (500 ml) followed by precipitation by adding diethyl ether. Filtration and air-drying the obtained solids gives 153 gm (93% yield) of the desired 1-[1-(4-chloro-phenyl)-cyclopropylmethyl]-1-ethyl-pyrrolidinium iodide as a white powder. The product is pure by 1H and 13C-NMR analysis.

Workup

  1. custom(equipped with a mechanical stirrer and a reflux condenser)
  2. temperaturethe mixture is heated
  3. temperatureat reflux for 3 hours
  4. temperatureThe reaction mixture is cooled down
  5. customexcess ethyl iodide and the solvent are removed at reduced pressure on a rotary evaporator
  6. customThe obtained dark tan-colored solids (162 gm) are further purified
  7. dissolutionby dissolving in acetone (500 ml)
  8. customfollowed by precipitation
  9. additionby adding diethyl ether
  10. filtrationFiltration
  11. customair-drying the obtained solids

Sources & evidence

ORD record
ord-080ea5b09abc45d198649afa9479cbed
Source dataset
uspto-grants-2006_03
Patent number
US07011811B2

Reaction notes

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