Diethylene Glycol → HCID 18965986, compound

HRID 2418986Notes

Reaction equation

HRID 2418986 reaction equation
C([NH:4][C:5]12[CH2:14][CH:10]([CH2:11][CH2:12][CH2:13]1)[CH:9]1[CH2:15][CH:6]2[CH2:7][CH2:8]1)(=O)C.[OH-].[Na+].C(O)COCCO>O>[NH2:4][C:5]12[CH2:14][CH:10]([CH2:11][CH2:12][CH2:13]1)[CH:9]1[CH2:15][CH:6]2[CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 8117Diethylene GlycolHCID 14798Sodium HydroxideHCID 53792494HCID 53792494, compound

Product 1

HCID 18965986HCID 18965986, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution comprising a mixture of 13.0 g (63 millimoles) of 1-acetylaminotricyclo [4.3.1.12,5 ] undecane of formula (II), 8.4 g (210 millimoles) of sodium hydroxide and 160 ml of diethylene glycol is refluxed under stirring for 15.5 hours. After allowing the solution to cool, the reaction solution is poured into water and is extracted with 200 ml of diethyl ether. The ether solution is washed with water and dried with anhydrous sodium sulfate. The ether is distilled out and the resulting residue is subjected to fractional distillation under reduced pressure to collect a fraction having a boiling point of 65°-66° C/1.0 mmHg. Thus 9.40 g (yield: 90.4%) of 1-aminotricyclo [4.3.1.12,5 ] undecane are obtained. After allowing the product to cool, white crystals of a melting point of 111°-113° C are obtained.

Workup

  1. temperatureis refluxed
  2. temperatureto cool
  3. extractionis extracted with 200 ml of diethyl ether
  4. washThe ether solution is washed with water
  5. dry with materialdried with anhydrous sodium sulfate
  6. distillationThe ether is distilled out
  7. distillationthe resulting residue is subjected to fractional distillation under reduced pressure
  8. customto collect a fraction

Sources & evidence

ORD record
ord-8779465cceb340ad9c0c8cf61f38fe13
Source dataset
uspto-grants-1978_08
Patent number
US04104305

Reaction notes

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