Triethylamine → HCID 12770913, compound
Reaction equation
Cl.[CH2:2]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([F:21])=[C:11]([N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[C:12]=2[F:14])[C:7](=[O:22])[C:6]([C:23]([OH:25])=[O:24])=[CH:5]1)[CH3:3].C(N(CC)CC)C.Br[CH2:34][CH2:35][OH:36]>CN(C=O)C>[CH2:2]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([F:21])=[C:11]([N:15]3[CH2:16][CH2:17][N:18]([CH2:34][CH2:35][OH:36])[CH2:19][CH2:20]3)[C:12]=2[F:14])[C:7](=[O:22])[C:6]([C:23]([OH:25])=[O:24])=[CH:5]1)[CH3:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
A mixture of 1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)quinoline-3-carboxylic acid hydrochloride (0.3 g), triethylamine (0.2 g), 2-bromoethanol (0.15 g), and DMF (5 ml) was heated with stirring at 90° C. for 3 hours. After the solvent evaporated, the residue was dissolved in 2N sodium hydroxide solution, neutralized with aqueous acetic acid, and extracted with dichloromethane. The organic layer was washed with water, dried over anhydrous sodium sulfate, and evaporated. The solid was recrystallized from a mixture of DMF and ethanol to give 1-ethyl-6,8-difluoro-1,4-dihydro-7-[4-(2-hydroxyethyl)-1-piperazinyl]-4-oxoquinoline-3-carboxylic acid (0.08 g), mp 225°-228° C.
Workup
- temperaturewas heated
- customAfter the solvent evaporated
- dissolutionthe residue was dissolved in 2N sodium hydroxide solution
- extractionextracted with dichloromethane
- washThe organic layer was washed with water
- dry with materialdried over anhydrous sodium sulfate
- customevaporated
- customThe solid was recrystallized from a mixture of DMF and ethanol
Sources & evidence
- ORD record
- ord-f78bf8ac75874b8b8db400af1e99407c
- Source dataset
- uspto-grants-1983_08
- Patent number
- US04398029
Reaction notes
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