Acetic Acid → HCID 54554601, compound

HRID 1578486Notes

Reaction equation

HRID 1578486 reaction equation
[NH2:1][N:2]1[CH2:7][CH2:6][N:5]([CH:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH:12]=[C:11]([C:19]#[N:20])[C:10]3[CH:21]=[CH:22][CH:23]=[CH:24][C:9]2=3)[CH2:4][CH2:3]1.[N:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH:31]=O.C(O)(=O)C>CC(O)C>[N:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH:31]=[N:1][N:2]1[CH2:3][CH2:4][N:5]([CH:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH:12]=[C:11]([C:19]#[N:20])[C:10]3[CH:21]=[CH:22][CH:23]=[CH:24][C:9]2=3)[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 142732-PyridinecarboxaldehydeHCID 12338802HCID 12338802, compound

Product 1

HCID 54554601HCID 54554601, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 40 parts of 5-(4-amino-1-piperazinyl)-5H-dibenzo[a,d]cycloheptene-10-carbonitrile, 50 parts of 2-pyridinecarboxaldehyde, 3 parts of glacial acetic acid, and 400 parts of 2-propanol is heated at the boiling point under reflux for 5 hours, then refrigerated until precipitation is complete. Insoluble solids are removed by filtration, consecutively washed with absolute ethanol and hexane, and air-dried. Recrystallization of this material from a mixture of chloroform and hexane affords 5-[4-(2-pyridylmethylene)amino-1-piperazinyl]-5H-dibenzo[a,d]cycloheptene- 10-carbonitrile as a light tan solid which, dried in air, melts at 182.5°-184°.

Workup

  1. temperatureis heated at the boiling point
  2. temperatureunder reflux for 5 hours
  3. customrefrigerated until precipitation
  4. customInsoluble solids are removed by filtration
  5. washconsecutively washed with absolute ethanol and hexane
  6. customair-dried
  7. customRecrystallization of this material
  8. additionfrom a mixture of chloroform and hexane

Sources & evidence

ORD record
ord-b90956b40a2e4158acdbed648e203f9d
Source dataset
uspto-grants-1976_02
Patent number
US03937701

Reaction notes

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