Ciprofloxacin → HCID 70393803, compound

HRID 1382210Notes

Reaction equation

HRID 1382210 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:20])=[C:11]([N:14]4[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]4)[CH:12]=3)[C:7](=[O:21])[C:6]([C:22]([OH:24])=[O:23])=[CH:5]2)[CH2:3][CH2:2]1.[CH2:25]([Br:28])[CH:26]=[CH2:27].C(N(CC)CC)C>CN(C)C=O>[BrH:28].[CH2:27]([N:17]1[CH2:18][CH2:19][N:14]([C:11]2[CH:12]=[C:13]3[C:8]([C:7](=[O:21])[C:6]([C:22]([OH:24])=[O:23])=[CH:5][N:4]3[CH:1]3[CH2:2][CH2:3]3)=[CH:9][C:10]=2[F:20])[CH2:15][CH2:16]1)[CH:26]=[CH2:25]

Participants

5

Reactant 3

HCID 2764CiprofloxacinHCID 7841Allyl bromideHCID 8471Triethylamine

Product 1

HCID 70393803HCID 70393803, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.3 g (10 mmol) of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid are heated at 60° C. in 50 ml of dimethylformamide with 1.8 g (15 mmol) of allyl bromide and 2.1 g of triethylamine for 8 hours. The mixture is concentrated in vacuo, the residue is stirred with 30 ml of water and the precipitate is filtered off with suction, washed with methanol and dried. 2.2 g of 7-(4-allyl-1-piperazinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid hydrobromide of melting point 295°-298° (with decomposition) are obtained; after recrystallization from water, 1.5 g of melting point 300°-302° (with decomposition) are isolated.

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. filtrationthe precipitate is filtered off with suction
  3. washwashed with methanol
  4. customdried

Sources & evidence

ORD record
ord-296d4d4908354960bb47e32d59ca155c
Source dataset
uspto-grants-1989_02
Patent number
US04806539

Reaction notes

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