Diethyl Ether → HCID 22992273, compound

HRID 1350114Notes

Reaction equation

HRID 1350114 reaction equation
[ClH:1].Cl.Cl.N[C:5]1[CH:6]=[C:7]([CH:11]2[CH2:16][CH:15]3[CH2:17][CH2:18][N:12]2[CH2:13][CH2:14]3)[CH:8]=[N:9][CH:10]=1.N([O:21][CH2:22][CH2:23]C(C)C)=O.C(OCC)C>C(O)C.C(Cl)(Cl)Cl>[ClH:1].[ClH:1].[CH2:22]([O:21][C:5]1[CH:6]=[C:7]([CH:11]2[CH2:16][CH:15]3[CH2:17][CH2:18][N:12]2[CH2:13][CH2:14]3)[CH:8]=[N:9][CH:10]=1)[CH3:23]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 8053Isoamyl NitriteHCID 22992270HCID 22992270, compound

Product 1

HCID 22992273HCID 22992273, compoundYield 81.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

To a stirred solution of 2-(5-amino-3-pyridyl)-1-azabicyclo[2.2.2]octane trihydrochloride (25 mg, 0.08 mmol) in dry ethanol (3 mL) was added isoamyl nitrite (0.10 mL, 0.74 mmol) and the mixture was refluxed for 2 h. When TLC analysis of the reaction mixture showed absence of starting material, the mixture was allowed to cool to ambient temperature. The solvent was removed by rotary evaporation to yield a thick brown oil, which solidified upon addition of dry diethyl ether. The product thus obtained was dissolved in chloroform and kept overnight at 4° C. to induce crystallization. The resulting solids were filtered, washed with diethyl ether and finally dried under vacuum for 24 h, to yield 2-(5-ethoxy-3-pyridyl)-1-azabicyclo[2.2.2]octane dihydrochloride (10 mg, 51%) as colorless needles.

Workup

  1. temperaturethe mixture was refluxed for 2 h
  2. customThe solvent was removed by rotary evaporation
  3. customto yield a thick brown oil, which
  4. customThe product thus obtained
  5. customcrystallization
  6. filtrationThe resulting solids were filtered
  7. washwashed with diethyl ether
  8. customfinally dried under vacuum for 24 h

Sources & evidence

ORD record
ord-0199084ed6c148d6af3ca7eb0c826e2e
Source dataset
uspto-grants-2007_05
Patent number
US07214686B2

Reaction notes

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