1-Piperazinecarboxaldehyde → HCID 14304585, compound

HRID 477013Notes

Reaction equation

[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([F:17])[C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1.[CH:22]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)=[O:23]>N1C=CC=CC=1>[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([F:17])[C:10]([F:16])=[C:11]([N:27]4[CH2:28][CH2:29][N:24]([CH:22]=[O:23])[CH2:25][CH2:26]4)[C:12]=3[F:14])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 1-cyclopropyl-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (2.0 g), 4-formylpiperazine (0.75 g), and pyridine (30 ml) was stirred at 50° C. for 1 hour. The reaction mixture was concentrated to dryness under reduced pressure. The residue was mixed with water and extracted with chloroform. The extract was dried, and chloroform was evaporated. Ethanol was added to the residue, and the precipitated crystals were collected by filtration. Recrystallization from chloroform-ethanol gave 1-cyclopropyl-5,6,8-trifluoro-7-(4-formyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (1.58 g), m.p. 290°-297° C.

Workup

concentrationThe reaction mixture was concentrated to dryness under reduced pressure
additionThe residue was mixed with water
extractionextracted with chloroform
customThe extract was dried
customchloroform was evaporated
additionEthanol was added to the residue
filtrationthe precipitated crystals were collected by filtration
customRecrystallization from chloroform-ethanol

Sources & evidence

ORD record: ord-0a3cfa4dd6f54e39beac71158c90bb25
Source dataset: uspto-grants-1989_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04886810

Reaction notes

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