Ethanol → HCID 67838308, compound

HRID 1077044Notes

Reaction equation

HRID 1077044 reaction equation
N(N=C([C:11]1[C:21]2[CH2:20][CH2:19][C:18]3[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=3[N:16](N=O)[C:15]=2[CH:14]=[CH:13][C:12]=1CC1C=CC=CC=1)C1C=CC=CC=1)=O.Cl.[NH:36]1[CH2:41][CH2:40][C:39](=O)[CH2:38][CH2:37]1.C(O)C>[Zn].C(O)(=O)C>[CH2:25]1[C:17]2[N:16]3[C:39]4[CH:40]=[CH:41][N:36]=[CH:37][C:38]=4[C:14]4[CH2:13][CH2:12][CH:11]=[C:21]([C:15]=43)[CH:20]=[CH:19][C:18]=2[CH2:22][CH2:23][CH2:24]1

Participants

6

Reactant 3

HCID 702EthanolHCID 30848514-Piperidone hydrochlorideHCID 86733463HCID 86733463, compound

Product 1

HCID 67838308HCID 67838308, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a mixture of 4.5 g of N-nitrosoiminodibenzyl (5-nitroso-10,11-dihydro-5H-dibenz[b,f]azepine), 6.0 g. of 4-piperidone hydrochloride and 6.5 g. of zinc dust in 30 ml. of absolute ethanol 12 ml. of glacial acetic acid are added dropwise, with constant stirring. Occasional cooling in an icebath is required to maintain the temperature at 20°-25° during the course of the reaction. After a little over 4 hours, the unchanged zinc is filtered off, washed with a minimum of absolute ethanol, and to the combined filtrate and wash there is added with stirring 8 ml. of concentrated sulfuric acid in 50 ml. of absolute ethanol. Stirring is continued while the mixture is warmed for about ten minutes, until the alcohol begins to reflux. It is then cooled down again; the inorganic insolubles are filtered off, and approximately 500 ml. of water is added to the filtrate, resulting in a voluminous white precipitate. The whole mixture is extracted with ether, and the residual aqueous phase is warmed up to transform the precipitate into granular solids, which are then filtered off and redissolved in approximately 600 ml. aqueous acetic acid. Some warming is required to completely dissolve all material. On treating this solution with 3N aqueous ammonia, the title compound is obtained as a tan-white granular solid, m.p. 134°-137°.

Workup

  1. temperatureOccasional cooling in an icebath
  2. temperatureto maintain the temperature at 20°-25°
  3. customduring the course of the reaction
  4. filtrationthe unchanged zinc is filtered off
  5. washwashed with a minimum of absolute ethanol
  6. washto the combined filtrate and wash there
  7. additionis added
  8. stirringStirring
  9. temperatureis warmed for about ten minutes, until the alcohol
  10. temperatureto reflux
  11. temperatureIt is then cooled down again
  12. filtrationthe inorganic insolubles are filtered off
  13. additionof water is added to the filtrate
  14. customresulting in a voluminous white precipitate
  15. extractionThe whole mixture is extracted with ether
  16. temperaturethe residual aqueous phase is warmed up
  17. filtrationare then filtered off
  18. dissolutionredissolved in approximately 600 ml
  19. dissolutionto completely dissolve all material
  20. additionOn treating this solution with 3N aqueous ammonia

Sources & evidence

ORD record
ord-d3336ff2b9b14e1e8e1931e2e5ffeca6
Source dataset
uspto-grants-1976_05
Patent number
US03959300

Reaction notes

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