1-Benzylpiperazine → 6H-Pyrido(2,3-b)(1,4)benzodiazepin-6-one, 5,11-dihydro-11-(1-oxo-3-(4-(phenylmethyl)-1-piperazinyl)propyl)-

HRID 2057897Notes

Reaction equation

HRID 2057897 reaction equation
Cl[CH2:2][CH2:3][C:4]([N:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[C:10](=[O:17])[NH:9][C:8]2[CH:18]=[CH:19][CH:20]=[N:21][C:7]1=2)=[O:5].[CH2:22]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(O)(C)C>[CH2:22]([N:29]1[CH2:34][CH2:33][N:32]([CH2:2][CH2:3][C:4]([N:6]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[C:10](=[O:17])[NH:9][C:8]3[CH:18]=[CH:19][CH:20]=[N:21][C:7]2=3)=[O:5])[CH2:31][CH2:30]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 759941-BenzylpiperazineHCID 1381057111-(3-chloropropionyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

Product 1

HCID 30532046H-Pyrido(2,3-b)(1,4)benzodiazepin-6-one, 5,11-dihydro-11-(1-oxo-3-(4-(phenylmethyl)-1-piperazinyl)propyl)-Yield 78%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 8.0 g of 11-(3-chloropropionyl)-5,11-dihydro-6H-pyrido-[2,3-b][1,4]-benzodiazepine-6-one and 30 ml of 1-benzyl-piperazine in 100 ml of isopropanol was refluxed for 1 hour. Then, the mixture was evaporated in vacuo to dryness and the residue was treated with sodium hydroxide solution. The base was extracted therefrom with chloroform and the chloroform extract was distilled to dryness. The residue was crystallized from xylene to obtain a 78% yield of 11-[3-(4-benzyl-1-piperazinyl)-propionyl]-5,11-dihydro-6H-pyrido-[2,3-b][1,4]-benzodiazepine-6-one with a melting point of 205°-207° C. The dihydro chloride salt of the acid base melted at 212°-214° C. after crystallization from methanol.

Workup

  1. temperaturewas refluxed for 1 hour
  2. customThen, the mixture was evaporated in vacuo to dryness
  3. additionthe residue was treated with sodium hydroxide solution
  4. extractionThe base was extracted
  5. extractionwith chloroform and the chloroform extract
  6. distillationwas distilled to dryness
  7. customThe residue was crystallized from xylene

Sources & evidence

ORD record
ord-7337acf4f366424fbde04eda97c8150c
Source dataset
uspto-grants-1980_07
Patent number
US04213985

Reaction notes

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