Norchlorcyclizine → HCID 19370338, compound

HRID 280850Notes

Reaction equation

HRID 280850 reaction equation
Br[CH2:2][CH2:3][CH2:4][N:5]1C(=O)C2=CC=CC=C2C1=O.[Cl:16][C:17]1[CH:35]=[CH:34][C:20]([CH:21]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH2:5][CH2:4][CH2:3][CH2:2][N:31]1[CH2:30][CH2:29][N:28]([CH:21]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:20]2[CH:19]=[CH:18][C:17]([Cl:16])=[CH:35][CH:34]=2)[CH2:33][CH2:32]1

Participants

5

Reactant 3

HCID 9340NorchlorcyclizineHCID 11430Potassium CarbonateHCID 21611N-3-Bromopropylphthalimide

Product 1

HCID 19370338HCID 19370338, compoundYield 102.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of N-(3-bromopropyl)phthalimide (26.8 g), 1-(4-chlorobenzhydryl)piperazine (28.6 g) and anhydrous potassium carbonate (13.8 g) in dimethylformamide (150 ml) was stirred at 70° C. for 2.5 hours. After being cooled to ambient temperature, the reaction mixture was poured into ice-water. The crystalline precipitate was collected by filtration, dried and dissolved in ethanol (800 ml). To the solution was added hydrazine hydrate (11.0 g) and the mixture was refluxed for 20 hours. The reaction mixture was hot-filtered and stood to cool. The obtained crystal was suspended in 10% hydrochloric acid (500 ml). The suspension was filtered and the filtrate was concentrated. The resultant residue was neutralized with aqueous sodium carbonate and extracted with chloroform. The extract was washed with water, dried and evaporated in vacuo to give 1-(3-aminopropyl)-4-(4-chlorobenzhydryl)piperazine (35.0 g) as an oil.

Workup

  1. temperatureAfter being cooled to ambient temperature
  2. filtrationThe crystalline precipitate was collected by filtration
  3. customdried
  4. dissolutiondissolved in ethanol (800 ml)
  5. additionTo the solution was added hydrazine hydrate (11.0 g)
  6. temperaturethe mixture was refluxed for 20 hours
  7. filtrationThe reaction mixture was hot-filtered
  8. temperatureto cool
  9. filtrationThe suspension was filtered
  10. concentrationthe filtrate was concentrated
  11. extractionextracted with chloroform
  12. washThe extract was washed with water
  13. customdried
  14. customevaporated in vacuo

Sources & evidence

ORD record
ord-55ecf7cf07e4465285851bfc40d4753b
Source dataset
uspto-grants-1986_05
Patent number
US04591590

Reaction notes

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