Water → HCID 12338802, compound

HRID 1578485Notes

Reaction equation

HRID 1578485 reaction equation
O.[N:2]([N:4]1[CH2:9][CH2:8][N:7]([CH:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH:14]=[C:13]([C:21]#[N:22])[C:12]3[CH:23]=[CH:24][CH:25]=[CH:26][C:11]2=3)[CH2:6][CH2:5]1)=O.[OH-].[NH4+]>[Zn].C(O)(=O)C>[NH2:2][N:4]1[CH2:5][CH2:6][N:7]([CH:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH:14]=[C:13]([C:21]#[N:22])[C:12]3[CH:23]=[CH:24][CH:25]=[CH:26][C:11]2=3)[CH2:8][CH2:9]1

Participants

6

Reactant 3

HCID 962WaterHCID 14923Ammonium HydroxideHCID 12338801HCID 12338801, compound

Product 1

HCID 12338802HCID 12338802, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Approximately 500 parts of water is slowly added to a solution of 98 parts of 5-(4-nitroso-1-piperazinyl)-5H-dibenzo[a,d]cycloheptene-10-carbonitrile in 1200 parts of glacial acetic acid. To the resultant mixture is added, at a rate such that the temperature does not exceed 35°, approximately 150 parts of zinc dust. When the addition is complete, the reaction mixture is stirred at 28°-30° for 1 hour, whereupon insoluble solids are filtered out and washed with 300 parts of 65% acetic acid. Washings and filtrate are combined and diluted with 3 volumes of water. The solution thus obtained is cooled to 5°-10° and maintained thereat while sufficient 30% ammonium hydroxide is added to induce alkalinity. The resultant mixture is extracted with chloroform. The chloroform extract is dried over anhydrous potassium carbonate and stripped of solvent by vacuum distillation. The residual viscous oil crystallizes from hexane to give 5-(4-amino-1-piperazinyl)-5H-dibenzo[a,d]cycloheptene-10-carbonitrile as a colorless solid which, dried in air, melts at 137°-146°.

Workup

  1. customdoes not exceed 35°
  2. additionWhen the addition
  3. filtrationare filtered out
  4. washwashed with 300 parts of 65% acetic acid
  5. additiondiluted with 3 volumes of water
  6. customThe solution thus obtained
  7. temperatureis cooled to 5°-10°
  8. temperaturemaintained
  9. extractionThe resultant mixture is extracted with chloroform
  10. extractionThe chloroform extract
  11. dry with materialis dried over anhydrous potassium carbonate
  12. distillationstripped of solvent by vacuum distillation
  13. customThe residual viscous oil crystallizes from hexane

Sources & evidence

ORD record
ord-5e249883e0ab4c3a820b5e58a449caca
Source dataset
uspto-grants-1976_02
Patent number
US03937701

Reaction notes

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