Octane → HCID 86734416, compound

HRID 1415157Notes

Reaction equation

HRID 1415157 reaction equation
FC1C=[CH:6][C:5]([CH:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[C:9]#[N:10])=CC=1.[C:17]1([CH3:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[NH2-:24].[Na+].CCCCCCCC>O>[N:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[CH:8]([CH2:5][CH2:6][N:24]1[CH2:23][CH:17]2[CH2:22][CH2:21][CH:20]1[CH2:19][CH2:18]2)[C:9]#[N:10]

Participants

6

Reactant 4

HCID 356OctaneHCID 1140Toluene2×HCID 24533Sodium amideHCID 10703742HCID 10703742, compound

Product 1

HCID 86734416HCID 86734416, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To solution of 41 parts of α-(4-fluorophenyl)-2-pyridinylacetonitrile (U.S. Pat. No. 3,225,054) in 350 parts of dry toluene is added 9 parts of sodamide and the mixture is stirred and heated at 90° C for 30 minutes. Heating is stopped and a solution of 40 parts of 2-(2-chloroethyl)-2-azabicyclo[2.2.2.]octane in 110 parts of dry toluene is added slowly over a period of 30 minutes. The mixture is stirred and refluxed for 6 hours before it is cooled and decomposed by the addition of water. The toluene layer is separated and washed with water and extracted with 6N hydrochloric acid. The extract is made alkaline and extracted with toluene. The toluene solution is washed with water and dried and the solvent is evaporated. Distillation provides 2-(4-fluorophenyl)-2-(2-pyridyl-4-(2-azabicyclo[2.2.2]oct-2-yl)butyronitrile. According to the procedure of Example 1 this nitrile is converted to 5-[1-(4-fluorophenyl)-1-(2-pyridyl)-3-(2-azabicyclo[2.2.2]-oct-2-yl)propyl]-1H-tetrazole and in turn to 5-[1-(4-fluorophenyl)-1-(2-pyridyl)-3-(2-azabicyclo[2.2.2.] oct-2-yl)propyl]-1,3,4-oxadiazole having the following structural formula. ##STR34##

Workup

  1. temperatureHeating
  2. stirringThe mixture is stirred
  3. temperaturerefluxed for 6 hours before it
  4. temperatureis cooled
  5. customThe toluene layer is separated
  6. washwashed with water
  7. extractionextracted with 6N hydrochloric acid
  8. extractionextracted with toluene
  9. washThe toluene solution is washed with water
  10. customdried
  11. customthe solvent is evaporated
  12. distillationDistillation

Sources & evidence

ORD record
ord-6d086122ec13449682d04365d7b08fe5
Source dataset
uspto-grants-1977_01
Patent number
US04003904

Reaction notes

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