Dabco → HCID 53634555, compound

HRID 1382214Notes

Reaction equation

HRID 1382214 reaction equation
[CH2:1]([N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.N12CCN(CC1)CC2.Cl[C:25]1[CH:34]=[C:33]2[C:28]([C:29](=[O:41])[C:30]([C:38]([OH:40])=[O:39])=[CH:31][N:32]2[CH:35]2[CH2:37][CH2:36]2)=[CH:27][C:26]=1[F:42]>CS(C)=O>[CH2:1]([N:10]1[CH2:15][CH2:14][N:13]([C:25]2[CH:34]=[C:33]3[C:28]([C:29](=[O:41])[C:30]([C:38]([OH:40])=[O:39])=[CH:31][N:32]3[CH:35]3[CH2:37][CH2:36]3)=[CH:27][C:26]=2[F:42])[CH2:12][CH2:11]1)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 9237DabcoHCID 86803CinnamylpiperazineHCID 483180Fluoroquinolonic acid

Product 1

HCID 53634555HCID 53634555, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2.1 g (10 mmol) of 1-cinnamyl-piperazine and 2.2 g of 1,4-diazabicyclo[2.2.2]octane are added to 2.8 g (10 mmol) of 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid in 35 ml of dimethyl sulphoxide, and the mixture is heated at 140° for 5 hours. It is concentrated under a high vacuum, the residue is stirred with 50 ml of water and the pH is brought to 6 with 2N hydrochloric acid. The precipitate which has separated out is filtered off with suction, washed with water and boiled up with methanol. 1.7 g of 7-(4-cinnamyl-1-piperazinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid of melting point 230°-234° (with decomposition) are obtained.

Workup

  1. temperaturethe mixture is heated at 140° for 5 hours
  2. concentrationIt is concentrated under a high vacuum
  3. customThe precipitate which has separated out
  4. filtrationis filtered off with suction
  5. washwashed with water

Sources & evidence

ORD record
ord-f7bb9e3478bd46b3b543573d8e3a78b5
Source dataset
uspto-grants-1989_02
Patent number
US04806539

Reaction notes

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