Sodium Hydroxide → 5H-Dibenz(b,f)azepine, 10-(2-(dimethylamino)ethyl)-5-methyl-

HRID 1076503Notes

Reaction equation

HRID 1076503 reaction equation
O[CH2:2][C:3]1([CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]([CH3:17])[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[OH-].[Na+]>C1(C)C=CC=C(C)C=1>[CH3:17][N:10]1[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[C:3]([CH2:18][CH2:19][N:20]([CH3:21])[CH3:22])=[CH:2][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]1=2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 14812Phosphorus oxide (P4O10)HCID 12813967HCID 12813967, compound

Product 1

HCID 2076725H-Dibenz(b,f)azepine, 10-(2-(dimethylamino)ethyl)-5-methyl-Yield 70%

Reagents, catalysts & solvents 1

HCID 7929M-XyleneSolvent

Procedure

A mixture of 24.5 gm of 9-hydroxymethyl-9-(β-dimethylaminoethyl)-10-methyl-acridane in a liter of m-xylene and 125 gm of phosphoric acid anhydride was heated at reflux for 3 hours and after cooling, the reaction mixture was poured over ice. The mixture was stirred for 15 minutes and was made alkaline by the addition of sodium hydroxide. The mixture was extracted with ethyl acetate and the ethyl acetate was washed with water, dried over magnesium sulfate and distilled to dryness in vacuo. The residue was dissolved in ether and the solution was filtered and concentrated to a small volume and pentane was added while distilling off the ether. After filtering, the filtrate was concentrated to about 100 cc and crystallization was started with icing for one hour. After filtering, the precipitate was washed with water and dried in vacuo to obtain 16 gm (70% yield) of 5-methyl-10-(β-dimethylaminoethyl)-dibenzo (b,f) azepine melting at 78°C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. temperatureafter cooling
  4. additionthe reaction mixture was poured over ice
  5. extractionThe mixture was extracted with ethyl acetate
  6. washthe ethyl acetate was washed with water
  7. dry with materialdried over magnesium sulfate
  8. distillationdistilled to dryness in vacuo
  9. dissolutionThe residue was dissolved in ether
  10. filtrationthe solution was filtered
  11. concentrationconcentrated to a small volume and pentane
  12. additionwas added
  13. distillationwhile distilling off the ether
  14. filtrationAfter filtering
  15. concentrationthe filtrate was concentrated to about 100 cc and crystallization
  16. waitwith icing for one hour
  17. filtrationAfter filtering
  18. washthe precipitate was washed with water
  19. customdried in vacuo

Sources & evidence

ORD record
ord-8be216812bc745158e1ff89b0f9d7ba5
Source dataset
uspto-grants-1976_05
Patent number
US03957757

Reaction notes

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