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

HRID 1649456Notes

Reaction equation

HRID 1649456 reaction equation
C1(C)C=CC(S(O[C:11]2[C:22]3=[C:23]4[N:18]([CH:19]([CH3:24])[CH2:20][CH2:21]3)[CH:17]=[C:16]([C:25]([OH:27])=[O:26])[C:15](=[O:28])[C:14]4=[CH:13][C:12]=2[Cl:29])(=O)=O)=CC=1.[F:31][C:32]([F:42])([F:41])[C:33]([N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1)=[O:34]>CS(C)=O>[F:42][C:32]([F:31])([F:41])[C:33]([N:35]1[CH2:40][CH2:39][N:38]([C:11]2[C:22]3=[C:23]4[N:18]([CH:19]([CH3:24])[CH2:20][CH2:21]3)[CH:17]=[C:16]([C:25]([OH:27])=[O:26])[C:15](=[O:28])[C:14]4=[CH:13][C:12]=2[Cl:29])[CH2:37][CH2:36]1)=[O:34]

Participants

4

Reactant 2

HCID 7172020TrifluoroacetylpiperazineHCID 204797438-(p-toluenesulfonyloxy)-9-chloro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid

Product 1

HCID 132695268-(4-trifluoroacetyl-1-piperazinyl)-9-chloro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acidYield 50%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 4.5 g of 8-(p-toluenesulfonyloxy)-9-chloro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid, 9.1 g of 1-trifluoroacetylpiperazine and 200 ml of anhydrous dimethyl sulfoxide was heated with stirring in an autoclave at 150° to 160° C. for 17 hours under nitrogen gas flow at a pressure of 10 atms. The reaction mixture was treated in the same manner as Example 73 to obtain 2.3 g of 8-(4-trifluoroacetyl-1-piperazinyl)-9-chloro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid as white rhombic crystals having a melting point of 300° C. or more.

Workup

  1. temperaturewas heated
  2. additionThe reaction mixture was treated in the same manner as Example 73

Sources & evidence

ORD record
ord-d81ef5879557425d8886424787a1915e
Source dataset
uspto-grants-1983_11
Patent number
US04416884

Reaction notes

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