Water → HCID 69583568, compound

HRID 6568Notes

Reaction equation

HRID 6568 reaction equation
[I-].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH2:12][N+:13]3([CH2:18][CH3:19])[CH2:17][CH2:16][CH2:15][CH2:14]3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[OH2:20]>>[OH-:20].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH2:12][N+:13]3([CH2:18][CH3:19])[CH2:17][CH2:16][CH2:15][CH2:14]3)[CH2:10][CH2:11]2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 962WaterHCID 695836481-{[1-(4-Chlorophenyl)cyclopropyl]methyl}-1-ethylpyrrolidin-1-ium iodide

Product 1

HCID 69583568HCID 69583568, compoundYield 96%

Procedure

The hydroxide form of 1-[1-(4-chloro-phenyl)-cyclopropyhnethyl]-1-ethyl-pyrrolidinium cation is obtained by an ion exchange treatment of the iodide salt with Ion-Exchange Resin-OH (BIO RAD® AH1-X8). In a 1-liter volume plastic bottle, 100 gm (255 mmol) of 1-[1-(4-chloro-phenyl)-cyclopropylmethyl]-1-ethyl-pyrrolidinium iodide is dissolved in 300 ml de-ionized water. Then, 320 gm of the ion exchange resin is added and the solution is allowed to gently stir overnight. The mixture is then filtered, and the resin cake is rinsed with minimal amount of de-ionized water. The filtrate is analyzed for hydroxide concentration by titration analysis on a small sample of the solution with 0.1N HCl. The reaction yields 96% of (245 mmol) of the desired 1-[1-(4-chloro-phenyl)-cyclopropylmethyl]-1-ethyl-pyrrolidinium hydroxide (hydroxide concentration of 0.6 M).

Workup

  1. filtrationThe mixture is then filtered
  2. washthe resin cake is rinsed with minimal amount of de-ionized water
  3. concentrationThe filtrate is analyzed for hydroxide concentration by titration analysis on a small sample of the solution with 0.1N HCl

Sources & evidence

ORD record
ord-3bcb5549129f4f7781a17099a365cfae
Source dataset
uspto-grants-2006_08
Patent number
US07083714B2

Reaction notes

Loading…