1-Benzyl 4-chloro-2,3,6,7-tetrahydro-5-oximinomethylene-1H-azepine hydrochloride → 1-Benzyl-4-chloro-5-cyano-2,3,6,7-tetrahydro-1H-azepine

HRID 1648925Notes

Reaction equation

HRID 1648925 reaction equation
Cl.[CH2:2]([N:9]1[CH2:15][CH2:14][C:13](=[C:16]=[N:17]O)[CH:12]([Cl:19])[CH2:11][CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>P(Cl)(Cl)(Cl)=O>[CH2:2]([N:9]1[CH2:15][CH2:14][C:13]([C:16]#[N:17])=[C:12]([Cl:19])[CH2:11][CH2:10]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 1

HCID 867391081-Benzyl 4-chloro-2,3,6,7-tetrahydro-5-oximinomethylene-1H-azepine hydrochloride

Product 1

HCID 130720321-Benzyl-4-chloro-5-cyano-2,3,6,7-tetrahydro-1H-azepine

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

43.5 gm (0.144 mol) of 1-benzyl-4-chloro-2,3,6,7-tetrahydro-5-oximinomethylene-1H-azepine hydrochloride were added to 450 ml of phosphorus oxychloride while stirring at ambient temperature. The mixture was then stirred for 3 hours more, and the reaction mixture was then allowed to stand overnight. Then, the excess phosphorus oxychloride was distilled off in a rotary evaporator, and the residue was carefully mixed with water while cooling with ice. While cooling was continued, the mixture was made slightly alkaline by the addition of concentrated ammonia, and an oil separated out which crystallized when scratched. The crystal slurry thus obtained was suction-filtered, washed with water, dried and recrystallized from isopropyl alcohol.

Workup

  1. stirringThe mixture was then stirred for 3 hours more
  2. distillationThen, the excess phosphorus oxychloride was distilled off in a rotary evaporator
  3. additionthe residue was carefully mixed with water
  4. temperaturewhile cooling with ice
  5. temperatureWhile cooling
  6. additionthe mixture was made slightly alkaline by the addition of concentrated ammonia
  7. customan oil separated out which
  8. customcrystallized when
  9. customThe crystal slurry thus obtained
  10. filtrationwas suction-filtered
  11. washwashed with water
  12. customdried
  13. customrecrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-97db7b5718574c90baa7b41876445999
Source dataset
uspto-grants-1983_11
Patent number
US04414225

Reaction notes

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