4-Aminopyridine → 3-(4-Pyridyl)-3-azaspiro[5,5]undecan-2,4-dione

HRID 127278Notes

Reaction equation

HRID 127278 reaction equation
[CH2:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C:2]21[CH2:12][C:11](=[O:13])[O:10][C:8](=O)[CH2:7]2.[NH2:14][C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1.C1(C)C(C)=CC=CC=1>O>[N:18]1[CH:19]=[CH:20][C:15]([N:14]2[C:8](=[O:10])[CH2:7][C:2]3([CH2:1][CH2:6][CH2:5][CH2:4][CH2:3]3)[CH2:12][C:11]2=[O:13])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 17274-AminopyridineHCID 7237O-XyleneHCID 27342891,1-Cyclohexanediacetic Anhydride

Product 1

HCID 128225403-(4-Pyridyl)-3-azaspiro[5,5]undecan-2,4-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The starting material is prepared as follows: The mixture of 25 g of 2,2-cyclohexane diacetic anhydride, 12.92 g of 4-aminopyridine, and 400 ml of xylene is refluxed for 25 hours using a water separator. The hot, supernatant xylene solution is decanted from an oil precipitate (which is discarded), cooled, filtered and the residue recrystallized from ethanol, to yield the 3-(4-pyridyl)-3-azaspiro[5,5]undecan-2,4-dione melting at 213°-215°.

Workup

  1. customThe starting material is prepared
  2. temperatureis refluxed for 25 hours
  3. customThe hot, supernatant xylene solution is decanted from an oil precipitate (which is discarded)
  4. temperaturecooled
  5. filtrationfiltered
  6. customthe residue recrystallized from ethanol

Sources & evidence

ORD record
ord-9b3b763cada94dab80b9d46af27a0b77
Source dataset
uspto-grants-1981_03
Patent number
US04255429

Reaction notes

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