Potassium Carbonate → HCID 15230394, compound

HRID 2226147Notes

Reaction equation

HRID 2226147 reaction equation
S(Cl)([Cl:3])=O.O[C:6]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH:11]2[CH2:12][CH2:13][N:8]([CH2:9][CH2:10]2)[CH2:7]1.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[Cl:3][C:6]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH:11]2[CH2:12][CH2:13][N:8]([CH2:9][CH2:10]2)[CH2:7]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 2085983-(Pyridin-2-yl)-1-azabicyclo[2.2.2]octan-3-ol

Product 1

HCID 15230394HCID 15230394, compoundYield 24.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (0.74 ml, 10.2 mmol) was added dropwise to a solution of 3-hydroxy-3-(2-pyridinyl)-1-azabicyclo[2.2.2]octane (1.04 g, 5.09 mmol, prepared as in Description 1) in dichloromethane (10 ml). The reaction mixture was stirred at room temperature for 1 h, poured into saturated aqueous potassium carbonate (30 ml) and extracted with dichloromethane. The organic extract was dried over magnesium sulphate and then concentrated to a brown oil. The crude product was chromatographed through silica-gel using dichloromethane/methanol/ammonia (94.5:5:0.5) as eluent to give first 0.28 g of 3-chloro-3-(2-pyridinyl)-1-azabicyclo[2.2.2]octane followed by 0.39 g of 3-(2-pyridinyl)-1-azabicyclo[2.2.2]oct-2-ene.

Workup

  1. extractionextracted with dichloromethane
  2. extractionThe organic extract
  3. dry with materialwas dried over magnesium sulphate
  4. concentrationconcentrated to a brown oil
  5. customThe crude product was chromatographed through silica-gel

Sources & evidence

ORD record
ord-d7e585b790df472cb40ef3631dcc3fcd
Source dataset
uspto-grants-1994_09
Patent number
US05346906

Reaction notes

Loading…