Sodium Hydroxide → 5H-Dibenz(b,f)azepine, 7-chloro-10-(2-(dimethylamino)ethyl)-5-methyl-

HRID 1076513Notes

Reaction equation

HRID 1076513 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]([CH2:22]O)([CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])[C:7]3[C:12]([N:13]([CH3:16])[C:14]=2[CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.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:3]=[CH:4][C:5]2[C:6]([CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])=[CH:22][C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:12]=3[N:13]([CH3:16])[C:14]=2[CH:15]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 14812Phosphorus oxide (P4O10)HCID 12813969HCID 12813969, compound

Product 1

HCID 2076765H-Dibenz(b,f)azepine, 7-chloro-10-(2-(dimethylamino)ethyl)-5-methyl-Yield 87.8%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 5 gm of 3-chloro-9-hydroxymethyl-9(β-dimethylaminoethyl)-10-methyl-acridane, 200 cc of xylene and 25 gm of phosphoric acid anhydride was refluxed for 3 hours with stirring and after cooling, the reaction mixture was poured over ice. The resulting mixture was made alkaline by the addition of 50 cc of sodium hydroxide solution and was extracted with ethyl acetate. The organic phase was washed with water, dried over magnesium sulfate and distilled to dryness in vacuo. The residue was subjected to chromatography over silica gel with elution with a 6-3-1 mixture of cyclohexane-chloroform-triethylamine. Evaporation of the solvent gave 4.15 gm of 7-chloro-5-methyl-10-(β-dimethylaminoethyl)-dibenzo (b,f) azepine. The product was amorphous and was soluble in alcohols, chlorinated solvents, ether and benzene and insoluble in water.

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperatureafter cooling
  3. additionthe reaction mixture was poured over ice
  4. extractionwas extracted with ethyl acetate
  5. washThe organic phase was washed with water
  6. dry with materialdried over magnesium sulfate
  7. distillationdistilled to dryness in vacuo
  8. washThe residue was subjected to chromatography over silica gel with elution with a 6-3-1 mixture of cyclohexane-chloroform-triethylamine
  9. customEvaporation of the solvent

Sources & evidence

ORD record
ord-1f172ea8437441368319176e935931ec
Source dataset
uspto-grants-1976_05
Patent number
US03957757

Reaction notes

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