Hydrochloric Acid → 8-(4-trifluoromethyl-1-piperazinyl)-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid hydrochloride

HRID 1649457Notes

Reaction equation

HRID 1649457 reaction equation
CS(O[C:6]1[C:17]2=[C:18]3[N:13]([CH2:14][CH2:15][CH2:16]2)[CH:12]=[C:11]([C:19]([OH:21])=[O:20])[C:10](=[O:22])[C:9]3=[CH:8][CH:7]=1)(=O)=O.[F:23][C:24]([F:32])([F:31])[N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.[ClH:33]>CS(C)=O>[ClH:33].[F:23][C:24]([F:32])([F:31])[N:25]1[CH2:30][CH2:29][N:28]([C:6]2[C:17]3=[C:18]4[N:13]([CH2:14][CH2:15][CH2:16]3)[CH:12]=[C:11]([C:19]([OH:21])=[O:20])[C:10](=[O:22])[C:9]4=[CH:8][CH:7]=2)[CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 128996808-methanesulfonyloxy-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acidHCID 227170471-(Trifluoromethyl)piperazine

Product 1

HCID 705295828-(4-trifluoromethyl-1-piperazinyl)-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 3.37 g of 8-methanesulfonyloxy-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid, 9.1 g of 1-trifluoromethylpiperazine and 200 ml of anhydrous dimethyl sulfoxide was heated with stirring in an autoclave at 170° to 180° C. for 20 hours under nitrogen gas flow at a pressure of 8 atms. The reaction mixture was treated in the same manner as in Example 73 and further treated with concentrated hydrochloric acid to obtain 1.7 g of 8-(4-trifluoromethyl-1-piperazinyl)-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid hydrochloride 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 in Example 73

Sources & evidence

ORD record
ord-b19115834d0f49b0983be4a0dc341bec
Source dataset
uspto-grants-1983_11
Patent number
US04416884

Reaction notes

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