Diethylene Glycol → HCID 20339673, compound

HRID 597228Notes

Reaction equation

HRID 597228 reaction equation
[C:1]1([CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:8][CH:9]2[C:14](=O)[CH:13]3[CH2:16][CH2:17][N:10]2[CH2:11][CH2:12]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].NN.C(O)COCCO>O>[C:18]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH:9]2[CH2:14][CH:13]3[CH2:16][CH2:17][N:10]2[CH2:11][CH2:12]3)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 8117Diethylene GlycolHCID 9321HydrazineHCID 14797Potassium HydroxideHCID 22759851HCID 22759851, compound

Product 1

HCID 20339673HCID 20339673, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

9.3 Parts 3-(2,2-diphenylethyl-1-azabicyclo[2.2.2]-octan-3-one, 1.30 parts potassium hydroxide, 3.6 parts by volume of an 85% solution of hydrazine in water, and 59 parts diethylene glycol are combined and refluxed, with stirring, under nitrogen for 2.75 hours. Stirring and heating are then discontinued and the reaction mixture is allowed to stand for 16 hours at which time the mixture is heated to distill until a head temperature of 235° C. is reached. After cooling to room temperature, the mixture is partitioned between 900 parts by volume of a 5% sodium chloride solution and two 430 parts portions of ether. The ethereal extracts are combined, washed with water, dried over anhydrous sodium sulfate and stripped in vacuo to give an oil which solidifies upon standing. This solid is crystallized from n-pentane to afford, as a white solid, 2-(2,2-diphenylethyl)-1-azabicyclo[2.2.2]-octane, melting at about 87.5°-89.0° C. This compound is represented by the following structural formula. ##STR10##

Workup

  1. temperaturerefluxed
  2. stirringStirring
  3. temperatureheating
  4. waitto stand for 16 hours at which time
  5. temperaturethe mixture is heated
  6. distillationto distill until a head temperature of 235° C.
  7. customthe mixture is partitioned between 900 parts by volume of a 5% sodium chloride solution and two 430 parts portions of ether
  8. washwashed with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. customto give an oil which
  11. customThis solid is crystallized from n-pentane

Sources & evidence

ORD record
ord-d62ae72dfa344ec9b8a1cc5ab9c53391
Source dataset
uspto-grants-1977_03
Patent number
US04013667

Reaction notes

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