HCID 131712268, compound → HCID 54332767, compound

HRID 1680665Notes

Reaction equation

HRID 1680665 reaction equation
[C:1]([CH2:6][CH2:7][CH2:8][CH:9]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]([CH2:20][CH2:21][CH2:22][N:23]([CH3:25])[CH3:24])[C:12]2[CH:26]=[CH:27][CH:28]=[CH:29][C:11]=2[C:10]1=O)([O:3][CH2:4][CH3:5])=[O:2]>C(O)(=O)C.[Pd]>[C:1]([CH2:6][CH2:7][CH2:8][CH:9]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]([CH2:20][CH2:21][CH2:22][N:23]([CH3:24])[CH3:25])[C:12]2[CH:26]=[CH:27][CH:28]=[CH:29][C:11]=2[CH2:10]1)([O:3][CH2:4][CH3:5])=[O:2]

Participants

4

Reactant 1

HCID 131712268HCID 131712268, compound

Product 1

HCID 54332767HCID 54332767, compoundYield 0.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

In a 150 ml glass hydrogenation vessel were placed 1 g (2.45 mole) of the 10-carboethoxypropyl-5-(3'-dimethylaminopropyl)-5H-dibenz[b,f]azepine-11-one prepared in Example 6 dissolved in 35 ml of glacial acetic acid and 1 g of 10% palladium on carbon. The vessel was placed on a Parr-pressure apparatus, flushed with nitrogen, evacuated, pressurized to 60 psi hydrogen and shaken for 4 days with daily pressure adjustment. The vessel was then flushed with nitrogen, evacuated, filtered through a Celite pad, washed with absolute methanol and concentrated on a rotary evaporator under reduced pressure. The residue was dissolved in chloroform and extracted with 10% NaHCO3 to remove excess acid. The organic phase was dried with magnesium sulfate, filtered and concentrated. The reaction was repeated on another 1 g lot of 10-carboethoxypropyl-5-(3'-dimethylaminopropyl)-5H-dibenz[b,f]azepine-11-one prepared in Example 6. The products were combined yielding 1.6 g crude material. The 1.6 g was applied to chromatographic plates (20-20 cm 2.5 mm prep tlc plates silica gel PF-254) and eluted with diethyl ether saturated with ammonia gas. The plates were air dried and developed four times until separation was maximized by UV inspection. The two bands were isolated, extracted with methanol, concentrated, redissolved in chloroform, filtered and concentrated on a rotary evaporator yielding 0.600 g of 10-carboethoxypropyl-5-(3'-dimethylaminopropyl)-10,11-dihydro-5H-dibenz[b,f]azepine and 0.805 g of starting material. The product (0.600 g) containing trace amounts of starting material was rechromatographed (using silica gel PF-254 20×20 cm 2.5 mm prep plates) and eluted with methanol:chloroform 1:9. The isolation procedure was the same as above.

Workup

  1. customIn a 150 ml glass hydrogenation vessel were placed
  2. customflushed with nitrogen
  3. customevacuated
  4. customThe vessel was then flushed with nitrogen
  5. customevacuated
  6. filtrationfiltered through a Celite pad
  7. washwashed with absolute methanol
  8. concentrationconcentrated on a rotary evaporator under reduced pressure
  9. dissolutionThe residue was dissolved in chloroform
  10. extractionextracted with 10% NaHCO3
  11. customto remove excess acid
  12. dry with materialThe organic phase was dried with magnesium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated
  15. customThe products were combined yielding 1.6 g crude material
  16. washeluted with diethyl ether saturated with ammonia gas
  17. customdried
  18. customuntil separation
  19. customThe two bands were isolated
  20. extractionextracted with methanol
  21. concentrationconcentrated
  22. dissolutionredissolved in chloroform
  23. filtrationfiltered
  24. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-218e0e8ab4174af196d5b6eef94fdbd0
Source dataset
uspto-grants-1981_06
Patent number
US04275160

Reaction notes

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