Diethylene Glycol → HCID 20339673, compound

HRID 1703812Notes

Reaction equation

HRID 1703812 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.CCCCC>[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

7

Reactant 4

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

Product 1

HCID 20339673HCID 20339673, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8003PentaneSolvent

Procedure

9.3 Parts of 2-(2,2-diphenylethyl-1-azabicyclo[2.2.2]octan-3-one, 1.3 parts of potassium hydroxide, 3.6 parts by volume of an 85% solution of hydrazine in water and 59 parts diethylene glycol are refluxed together, with stirring, under nitrogen for 2.75 hours. Stirring and heating are then discontinued and the reaction mixture is allowed to stand overnight. The mixture is then heated to distill under nitrogen until a head temperature of 235° C. is reached. After cooling to room temperature, the mixture is partitioned between 900 parts by volume of 5% sodium chloride solution and two 600 parts by volume portions of ethyl ether. The ethereal extracts are combined, washed with water, dried over anhydrous sodium sulfate and stripped in vacuo to give an residual oil which solidifies upon standing. This solid is dissolved in 300 parts by volume of hot n-pentane. The solution is then concentrated on the steam bath to 45 parts by volume and cooled to room temperature to give a solid precipitate which is filtered off, washed with n-pentane and dried in vacuo to give a white solid 2-(2,2-diphenylethyl)-1-azabicyclo[2.2.2]octane, melting at about 87.5°-89° C. This compound is represented by the following structural formula ##STR4##

Workup

  1. stirringStirring
  2. temperatureheating
  3. waitto stand overnight
  4. temperatureThe mixture is then heated
  5. distillationto distill under nitrogen until a head temperature of 235° C.
  6. customthe mixture is partitioned between 900 parts by volume of 5% sodium chloride solution and two 600 parts by volume portions of ethyl ether
  7. washwashed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. customto give an residual oil which
  10. concentrationThe solution is then concentrated on the steam bath to 45 parts by volume
  11. temperaturecooled to room temperature
  12. customto give a solid precipitate which
  13. filtrationis filtered off
  14. washwashed with n-pentane
  15. customdried in vacuo

Sources & evidence

ORD record
ord-597dd95cece546ac9f30778d992a7357
Source dataset
uspto-grants-1978_11
Patent number
US04125531

Reaction notes

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