1-(2-Propynyl)piperazine → 8-[4-(2-propynyl)-1-piperazinyl]-9-chloro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid

HRID 1649454Notes

Reaction equation

HRID 1649454 reaction equation
Cl[C:2]1[C:13]2=[C:14]3[N:9]([CH:10]([CH3:15])[CH2:11][CH2:12]2)[CH:8]=[C:7]([C:16]([OH:18])=[O:17])[C:6](=[O:19])[C:5]3=[CH:4][C:3]=1[Cl:20].[CH2:21]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)[C:22]#[CH:23]>CN(P(N(C)C)(N(C)C)=O)C>[CH2:21]([N:24]1[CH2:29][CH2:28][N:27]([C:2]2[C:13]3=[C:14]4[N:9]([CH:10]([CH3:15])[CH2:11][CH2:12]3)[CH:8]=[C:7]([C:16]([OH:18])=[O:17])[C:6](=[O:19])[C:5]4=[CH:4][C:3]=2[Cl:20])[CH2:26][CH2:25]1)[C:22]#[CH:23]

Participants

4

Reactant 2

HCID 146273691-(2-Propynyl)piperazineHCID 155717798,9-dichloro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid

Product 1

HCID 132695278-[4-(2-propynyl)-1-piperazinyl]-9-chloro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acidYield 58.5%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 1.6 g of 8,9-dichloro-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid, 3.2 g of 1-propargylpiperazine and 25 ml of HMPTA was heated with stirring at 160° C. for 5 hours under atmosphere of argon. After completion of the reaction, the solvent was removed by distillation and the residue was washed with water. The residue was dissolved in 100 ml of water and insoluble substances were removed by filtration. The aqueous fraction was extracted with 200 ml of chloroform and the chloroform fraction was dried over anhydrous sodium sulfate. After concentration, the concentrate was purified through a silica gel column chromatography (silica gel: Wako C-200, a trade name for a product of Wako Junyako Co., Ltd.; eluent: chloroform-methanol (9:1 by volume)) to obtain 1.2 g of 8-[4-(2-propynyl)-1-piperazinyl]-9-chloro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid having a melting point of 211° to 213° C.

Workup

  1. temperaturewas heated
  2. customAfter completion of the reaction
  3. customthe solvent was removed by distillation
  4. washthe residue was washed with water
  5. dissolutionThe residue was dissolved in 100 ml of water
  6. custominsoluble substances were removed by filtration
  7. extractionThe aqueous fraction was extracted with 200 ml of chloroform
  8. dry with materialthe chloroform fraction was dried over anhydrous sodium sulfate
  9. concentrationAfter concentration
  10. customthe concentrate was purified through a silica gel column chromatography (silica gel

Sources & evidence

ORD record
ord-355450c296e44c18a8f86fcc5c4774e4
Source dataset
uspto-grants-1983_11
Patent number
US04416884

Reaction notes

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