3-Aminopyridine → 8-(3-Pyridyl)-8-azaspiro[4,5]decan-7,9-dione

HRID 1105687Notes

Reaction equation

HRID 1105687 reaction equation
[CH2:1]1[CH2:5][C:4]2([CH2:12][C:10](=[O:11])[O:9][C:7](=O)[CH2:6]2)[CH2:3][CH2:2]1.[NH2:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1>C1(C)C(C)=CC=CC=1>[N:16]1[CH:17]=[CH:18][CH:19]=[C:14]([N:13]2[C:7](=[O:9])[CH2:6][C:4]3([CH2:3][CH2:2][CH2:1][CH2:5]3)[CH2:12][C:10]2=[O:11])[CH:15]=1

Participants

4

Reactant 2

HCID 100093-AminopyridineHCID 79743Cyclopentane-1,1-diacetic anhydride

Product 1

HCID 126505138-(3-Pyridyl)-8-azaspiro[4,5]decan-7,9-dione

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

The starting material is prepared as follows. The mixture of 16.8 g of 3,3-tetramethyleneglutaric anhydride, 9.4 g of 3-aminopyridine and 225 ml of xylene is stirred and refluxed for 48 hours while collecting the water formed. After cooling in the refrigerator the precipitate obtained is filtered off and recrystallized from 300 ml ethanol-hexane, to yield the 8-(3-pyridyl)-8-azaspiro[4,5]decan-7,9-dione melting at 153°-154°.

Workup

  1. customThe starting material is prepared
  2. temperaturerefluxed for 48 hours
  3. customwhile collecting the water
  4. customformed
  5. temperatureAfter cooling in the refrigerator the precipitate
  6. customobtained
  7. filtrationis filtered off
  8. customrecrystallized from 300 ml ethanol-hexane

Sources & evidence

ORD record
ord-dc47ebac21da42e085fa5d17ea2c3d80
Source dataset
uspto-grants-1982_01
Patent number
US04309541

Reaction notes

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