2-(4-methoxyphenyl)piperazine → HCID 54470582, compound

HRID 344907Notes

Reaction equation

HRID 344907 reaction equation
[CH:1]1([N:4]2[C:13]3[N:12]=[C:11]4[CH:14]=[C:15](F)[C:16]([F:18])=[CH:17][C:10]4=[CH:9][C:8]=3[C:7](=[O:20])[C:6]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:5]2)[CH2:3][CH2:2]1.[CH3:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([CH:34]2[NH:39][CH2:38][CH2:37][NH:36][CH2:35]2)=[CH:30][CH:29]=1>CS(C)=O>[CH:1]1([N:4]2[C:13]3[N:12]=[C:11]4[CH:14]=[C:15]([N:36]5[CH2:37][CH2:38][NH:39][CH:34]([C:31]6[CH:32]=[CH:33][C:28]([O:27][CH3:26])=[CH:29][CH:30]=6)[CH2:35]5)[C:16]([F:18])=[CH:17][C:10]4=[CH:9][C:8]=3[C:7](=[O:20])[C:6]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:5]2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 27717532-(4-methoxyphenyl)piperazineHCID 148533401-Cyclopropyl-3-ethoxycarbonyl-7,8-difluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine

Product 1

HCID 54470582HCID 54470582, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 1-cyclopropyl-3-ethoxycarbonyl-7,8-difluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine (2 g) and (RS)-3-(4-methoxyphenyl)piperazine (2.3 g) in dimethyl sulphoxide (20 cc) is heated to a temperature in the region of 90° C. for 1 hour and a half. After cooling to approximately 20° C., the insoluble matter is drained, washed with water (3×15 cc) and recrystallized in a mixture of ethanol (100 cc) and dimethylformamide (25 cc). (RS)-1-Cyclopropyl-3-ethoxycarbonyl-7-fluoro-8-[3-(4-methoxyphenyl)-1-piperazinyl]-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine (2.1 g) is obtained in the form of a yellow solid, m.p. 199° C.

Workup

  1. temperatureAfter cooling to approximately 20° C.
  2. washwashed with water (3×15 cc)
  3. customrecrystallized in a mixture of ethanol (100 cc) and dimethylformamide (25 cc)

Sources & evidence

ORD record
ord-9d2d931f61ac40949b4da1b73f1557e4
Source dataset
uspto-grants-1991_10
Patent number
US05053509

Reaction notes

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