Sodium Carbonate → 5,11-dihydro-11-[3-(4-prenyl-1-piperazinyl)-propionyl]-6H-pyrido-[2,3-b][1,4]-benzodiazepine-6-one

HRID 2057896Notes

Reaction equation

HRID 2057896 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].C(=O)([O-])[O-].[Na+].[Na+].[CH2:28]([N:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1)[CH:29]=[C:30]([CH3:32])[CH3:31]>C(O)C>[CH2:28]([N:33]1[CH2:34][CH2:35][N:36]([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])[CH2:37][CH2:38]1)[CH:29]=[C:30]([CH3:32])[CH3:31]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 104419041-(3-Methyl-but-2-enyl)-piperazineHCID 1381057111-(3-chloropropionyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

Product 1

HCID 203293845,11-dihydro-11-[3-(4-prenyl-1-piperazinyl)-propionyl]-6H-pyrido-[2,3-b][1,4]-benzodiazepine-6-oneYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6.6 g of 11-(3-chloropropionyl)-5,11-dihydro-6H-pyrido-[2,3-b][1,4]-benzodiazepine-6-one, 2.56 g of sodium carbonate and 4.0 g of 1-prenylpiperazine was refluxed in 90 ml of absolute ethanol for 2 hours. Then, the reaction mixture was vacuum filtered while still hot and the filtrate was evaporated to a volume of about 20 ml. The crystallized precipitate was vacuum filtered and the product was crystallized from isopropanol to obtain a 62% yield of 5,11-dihydro-11-[3-(4-prenyl-1-piperazinyl)-propionyl]-6H-pyrido-[2,3-b][1,4]-benzodiazepine-6-one melting at 199°-201° C.

Workup

  1. filtrationfiltered while still hot and the filtrate
  2. customwas evaporated to a volume of about 20 ml
  3. filtrationfiltered
  4. customthe product was crystallized from isopropanol

Sources & evidence

ORD record
ord-4ca4b30eef0d483cac15571226520bbc
Source dataset
uspto-grants-1980_07
Patent number
US04213985

Reaction notes

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