Piperazine → HCID 67828803, compound

HRID 1494397Notes

Reaction equation

HRID 1494397 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C:7](=O)[CH2:6][CH2:5]2.[NH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1>C1(C)C=CC=CC=1>[ClH:1].[ClH:1].[N:13]1([CH:7]2[CH2:6][CH2:5][C:4]3[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=3)[CH2:8]2)[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 44561396-Chloro-2-tetralone

Product 1

HCID 67828803HCID 67828803, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture consisting of 6-chloro-2-tetralone (5.41 g), piperazine (5.16 g), and 4A molecular sieves (8 g) in 100 ml of dry toluene was heated at reflux with stirring for a short period of time under nitrogen. The toluene was evaporated, and 100 ml of THF and 10 ml of methanol were added to the residue. Sodium cyanoborohydride (1.86 g) was added, the solution was stirred in the cold under nitrogen, and gaseous HCl was added portionwise periodically above the surface until the reaction solution remained acidic. After stirring at room temperature overnight, the sieves were filtered off, and the filtrate was evaporated to dryness. The residue was partitioned between 1N HCl and ether; the aqueous phase was separated and extracted twice with ether. The solution was made basic with sodium hydroxide. The oil which formed was extracted into ether, and the ether solution was dried over Na2SO4. Evaporation of the ether left of a solid (5.1 g). A solution of the solid in ethanol was treated with excess gaseous HCl. After chilling for a period of time, the crystals which had separated were filtered and washed with ethanol. After recrystallization from methanol there was obtained 2.64 g of the title compound. m.p. 264-265° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. customThe toluene was evaporated
  4. addition100 ml of THF and 10 ml of methanol were added to the residue
  5. additionSodium cyanoborohydride (1.86 g) was added
  6. stirringthe solution was stirred in the cold under nitrogen, and gaseous HCl
  7. additionwas added portionwise periodically above the surface until the reaction solution
  8. stirringAfter stirring at room temperature overnight
  9. filtrationthe sieves were filtered off
  10. customthe filtrate was evaporated to dryness
  11. customThe residue was partitioned between 1N HCl and ether
  12. customthe aqueous phase was separated
  13. extractionextracted twice with ether
  14. customThe oil which formed
  15. extractionwas extracted into ether
  16. dry with materialthe ether solution was dried over Na2SO4
  17. customEvaporation of the ether
  18. waitleft of a solid (5.1 g)
  19. additionA solution of the solid in ethanol was treated with excess gaseous HCl
  20. temperatureAfter chilling for a period of time
  21. customthe crystals which had separated
  22. filtrationwere filtered
  23. washwashed with ethanol
  24. customAfter recrystallization from methanol

Sources & evidence

ORD record
ord-47fe5cf6d18a4cd4a2eec9aa94adf00f
Source dataset
uspto-grants-1991_06
Patent number
US05026707

Reaction notes

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