Hexahydro-1,4-diazepine → HCID 67828956, compound

HRID 1494400Notes

Reaction equation

HRID 1494400 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[CH2:19][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)[CH2:19][CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 68163Hexahydro-1,4-diazepineHCID 44561396-Chloro-2-tetralone

Product 1

HCID 67828956HCID 67828956, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 6-chloro-2-tetralone (7.22 g) and homopiperazine (8.0 g) in 100 ml of toluene were added 10 g of 3A molecular sieves. The mixture was heated on the steam bath for 2 hours, the sieves were filtered off, and toluene was evaporated from the filtrate. The residue was dissolved in a mixture of 100 ml of THF and 30 ml of methanol. The resultant solution was cooled in an ice bath with stirring under nitrogen, 2.51 g of sodium cyanoborohydride were added, and, with stirring and cooling, gaseous HCl was added portionwise periodically until the solution remained acidic. After stirring overnight at room temperature, the solvents were evaporated, and the residue was partitioned between dilute hydrochloric acid and ether. The acidic aqueous layer was separated and made basic with sodium hydroxide. The oil which formed was extracted with ether. The ether solution was dried (MgSO4), and the ether was evaporated. The residue was dissolved in ethanol, and excess gaseous HCl was added to the solution The solvent was evaporated. The residue crystallized slowly from a mixture of ethanol and ether to obtain 3.22 g of the title compound. m.p. 181°-183° C.

Workup

  1. temperatureThe mixture was heated on the steam bath for 2 hours
  2. filtrationthe sieves were filtered off
  3. customtoluene was evaporated from the filtrate
  4. dissolutionThe residue was dissolved in a mixture of 100 ml of THF and 30 ml of methanol
  5. temperatureThe resultant solution was cooled in an ice bath
  6. addition2.51 g of sodium cyanoborohydride were added
  7. stirringwith stirring
  8. temperaturecooling
  9. additiongaseous HCl was added portionwise periodically until the solution
  10. stirringAfter stirring overnight at room temperature
  11. customthe solvents were evaporated
  12. customthe residue was partitioned between dilute hydrochloric acid and ether
  13. customThe acidic aqueous layer was separated
  14. customThe oil which formed
  15. extractionwas extracted with ether
  16. dry with materialThe ether solution was dried (MgSO4)
  17. customthe ether was evaporated
  18. dissolutionThe residue was dissolved in ethanol
  19. additionexcess gaseous HCl was added to the solution The solvent
  20. customwas evaporated
  21. customThe residue crystallized slowly from a mixture of ethanol and ether

Sources & evidence

ORD record
ord-8b49d999f2e64b5cb62377e3c35e1eb3
Source dataset
uspto-grants-1991_06
Patent number
US05026707

Reaction notes

Loading…