Hydrazine hydrate (1:1) → 5H-Dibenzo[a,d]cycloheptene-5-propanamine

HRID 1284231Notes

Reaction equation

HRID 1284231 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][CH2:8][CH:9]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[CH:13]=[CH:12][C:11]3[CH:20]=[CH:21][CH:22]=[CH:23][C:10]2=3)C(=O)C2=CC=CC=C12.O.NN>C(O)C>[NH2:5][CH2:6][CH2:7][CH2:8][CH:9]1[C:10]2[CH:23]=[CH:22][CH:21]=[CH:20][C:11]=2[CH:12]=[CH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]1=2

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 214121125-(3-phthalimidopropyl)-5H-dibenzo[a,d]cycloheptene

Product 1

HCID 214120995H-Dibenzo[a,d]cycloheptene-5-propanamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-(3-Phthalimidopropyl)-5H-dibenzo[a,d]cycloheptene, 2.15 g. (0.0054 mole), is dissolved in 50 ml. of hot 95% ethanol. Hydrazine hydrate, 0.6 ml., is added and the solution heated to refluxing for 2 hours. The solution then is cooled, acidified, and the precipitate of phthalhydrazide removed by filtration. Ethanol is distilled from the filtrate under reduced pressure and the residue dissolved in 40 ml. of water. The filtered solution is evaporated by heating under reduced pressure to a volume of approximately 20 ml. Upon cooling, the hydrochloride salt of 5-(3-aminopropyl)-5H-dibenzo[a,d]cycloheptene is precipitated in a yield of 1.35 g. (87.5%). After recrystallization from a mixture of ethanol and ether and from isopropyl alcohol, an analytical sample melted at 263°-265°C., dec.

Workup

  1. dissolution(0.0054 mole), is dissolved in 50 ml
  2. addition, is added
  3. temperaturethe solution heated
  4. temperatureto refluxing for 2 hours
  5. temperatureThe solution then is cooled
  6. customthe precipitate of phthalhydrazide removed by filtration
  7. distillationEthanol is distilled from the filtrate under reduced pressure
  8. dissolutionthe residue dissolved in 40 ml
  9. customThe filtered solution is evaporated
  10. temperatureby heating under reduced pressure to a volume of approximately 20 ml
  11. temperatureUpon cooling
  12. customthe hydrochloride salt of 5-(3-aminopropyl)-5H-dibenzo[a,d]cycloheptene is precipitated in a yield of 1.35 g
  13. customAfter recrystallization
  14. additionfrom a mixture of ethanol and ether

Sources & evidence

ORD record
ord-f4b5b2224cd247568e8888ccf12f4c1c
Source dataset
uspto-grants-1976_08
Patent number
US03978121

Reaction notes

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