Water → HCID 70057865, compound

HRID 1602186Notes

Reaction equation

HRID 1602186 reaction equation
[Br-:1].O[CH:3]1[CH:8]2[CH2:9][CH2:10][N+:5]([CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])([CH2:6][CH2:7]2)[CH2:4]1.[H-].[Na+].IC.O.[CH3:21][O:22]CCOC>>[Br-:1].[CH3:21][O:22][CH:6]1[CH2:7][CH:8]2[CH2:9][CH2:10][N+:5]1([CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH2:4][CH2:3]2

Participants

6

Reactant 5

HCID 962WaterHCID 6328Methyl iodideHCID 80711,2-DimethoxyethaneHCID 24758Sodium hydrideHCID 69955297HCID 69955297, compound

Product 1

HCID 70057865HCID 70057865, compoundYield 100%

Procedure

To a suspension of (±)-3-hydroxy-1-pentylquinuclidinium bromide (20 g, 72 mmol) in dry 1,2-dimethoxyethane (150 ml) at 0° C., under nitrogen, was added sodium hydride (3.48 g, 60% in mineral oil, 86.8 mmol) and then iodomethane (11.3 ml, 181 mmol). The temperature was allowed to rise to room temperature overnight. Water (200 ml) was added and the mixture was extracted with 6×100 ml dichloromethane. Drying and evaporation gave an oily residue which, after trituration with petrol ether, gave the title compound as a crystalline solid. Yield 23.9 g (That the yield was more than 100% is explained by the fact that there is a mixture of bromide and iodide as counter ions.).

Workup

  1. extractionthe mixture was extracted with 6×100 ml dichloromethane
  2. customDrying
  3. customevaporation
  4. customgave an oily residue which

Sources & evidence

ORD record
ord-fdbe6d33cf6b4248b1a6086ee8d5a632
Source dataset
uspto-grants-1999_11
Patent number
US05981539

Reaction notes

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