Isopropanol → HCID 21094261, compound

HRID 1350115Notes

Reaction equation

HRID 1350115 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(OCCC(C)C)=O.C(Cl)(Cl)[Cl:28].[CH:31]([OH:34])([CH3:33])[CH3:32]>>[ClH:28].[ClH:1].[CH:31]([O:34][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)([CH3:33])[CH3:32]

Participants

5

Reactant 4

HCID 3776IsopropanolHCID 6212ChloroformHCID 8053Isoamyl NitriteHCID 22992270HCID 22992270, compound

Product 1

HCID 21094261HCID 21094261, compoundYield 55%

Procedure

To a stirred solution of 2-(5-amino-3-pyridyl)-1-azabicyclo[2.2.2]octane trihydrochloride (50 mg, 0.16 mmol) in dry isopropanol (5 mL) was added isoamyl nitrite (0.1 mL, 0.97 mmol) and the reaction mixture was refluxed for 2 h. When TLC analysis of the reaction mixture showed the absence of starting material, the mixture was allowed to warm to ambient temperature and then the solvent was removed under vacuum. A white solid was obtained upon the addition of dry diethyl ether. The solid was dissolved with heating in a minimum amount of chloroform, and the solution kept over night at 4° C. to induce crystallization. The solid thus obtained was filtered and dried under vacuum for 24 h to afford 2-(5-isopropoxy-3-pyridyl)-1-azabicyclo[2.2.2]octane dihydrochloride (28 mg, 55%) as colorless needles.

Workup

  1. temperaturethe reaction mixture was refluxed for 2 h
  2. customthe solvent was removed under vacuum
  3. customA white solid was obtained upon the addition of dry diethyl ether
  4. dissolutionThe solid was dissolved
  5. waitthe solution kept over night at 4° C.
  6. customcrystallization
  7. customThe solid thus obtained
  8. filtrationwas filtered
  9. customdried under vacuum for 24 h

Sources & evidence

ORD record
ord-a20734fb194e4f9eaa6a117c59859d07
Source dataset
uspto-grants-2007_05
Patent number
US07214686B2

Reaction notes

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