Sodium Hydroxide → 5H-Dibenz(b,f)azepine, 8-chloro-10-(2-(dimethylamino)ethyl)-5-methyl-

HRID 1076510Notes

Reaction equation

HRID 1076510 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[N:12]([CH3:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([CH2:22]O)([CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])[C:4]=2[CH:3]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[OH-].[Na+]>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[N:12]([CH3:16])[C:11]3[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=3[CH:22]=[C:5]([CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 14812Phosphorus oxide (P4O10)HCID 12813968HCID 12813968, compound

Product 1

HCID 2076745H-Dibenz(b,f)azepine, 8-chloro-10-(2-(dimethylamino)ethyl)-5-methyl-Yield 82.5%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 5 gm of 2-chloro-9-hydroxymethyl-9-(β-dimethylaminoethyl)-10-methyl-acridane, 150 cc of xylene and 25 gm of phosphoric acid anhydride was refluxed for 3 hours under a nitrogen atmosphere and after cooling, the reaction mixture was poured into a water-ice mixture. The mixture was made alkaline by the addition of 35cc sodium hydroxide solution and was extracted with ethyl acetate. The organic phase was washed with an aqueous sodium chloride solution, dried over magnesium sulfate, treated with charcoal, filtered and evaporated to dryness to obtain 3.9 gm of raw 8-chloro-5-methyl-10-(β-dimethylaminoethyl)dibenzo (b,f) azepine. The 3.9 gm of raw product were dissolved in 15 cc of methanol and a solution of 1.2 gm of fumaric acid in 45 cc of methanol was added thereto. The methanol was distilled off and replaced with ethyl acetate and the mixture was then refrigerated for 48 hours for crystallization and filtered. The precipitate was washed with ethyl acetate and dried to obtain 2.8 gm, fumarate of 8-chloro-5-methyl-10-(β-dimethylaminoethyl)-dibenzo (b,f) azepine melting at 150°C, then 164°C. Cooling of the mother liquors gave a second crop of 0.25 g of product.

Workup

  1. temperaturewas refluxed for 3 hours under a nitrogen atmosphere
  2. temperatureafter cooling
  3. extractionwas extracted with ethyl acetate
  4. washThe organic phase was washed with an aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. additiontreated with charcoal
  7. filtrationfiltered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-c51c56cf6ebf4a13a39f8cb8ba430ee7
Source dataset
uspto-grants-1976_05
Patent number
US03957757

Reaction notes

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