1-Methylpiperazine → Hydrochloric Acid

HRID 652053Notes

Reaction equation

HRID 652053 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8][N:9]2[CH:12]2[CH2:14][CH2:13]2)=[CH:4][N:3]=1.[CH3:19][N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1>C(O)C.CS(C)=O>[CH3:19][N:20]1[CH2:25][CH2:24][N:23]([C:2]2[CH:11]=[C:10]3[C:5]([C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8][N:9]3[CH:12]3[CH2:14][CH2:13]3)=[CH:4][N:3]=2)[CH2:22][CH2:21]1.[ClH:1]

Participants

6

Reactant 2

HCID 531671-MethylpiperazineHCID 130419067-Chloro-1-cyclopropyl-4-oxo-1,4-dihydro-1,6-naphthyridine-3-carboxylic acid

Product 2

HCID 313Hydrochloric AcidHCID 13041907HCID 13041907, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Procedure

A suspension of 2.64 g of 7-chloro-1-cyclopropyl-4-oxo-1,4-dihydro-1,6-naphthyridine-3-carboxylic acid and 2.5 g of N-methylpiperazine in 30 ml of ethanol or DMSO (=Dimethylsulfoxide) was heated to the boiling point under reflux for 16 hours or to 135°-140° C. for two hours. The diluent was distilled off in vacuo, the residue was dissolved in 30 ml of 1N NaOH, the solution was filtered and the filtrate was acidified with 10 strength hydrochloric acid. The precipitate was filtered off and washed with water and ethanol. It could be recrystallised from N-dimethylformamide/ethanol. 3.1 g (94% of the theoretical yield) of 7-(4-methylpiperazino)-1-cyclopropyl-4-oxo-1,4-dihydro-1,6-naphthyridine-3-carboxylic acid of melting point 326° C. (hydrochloride) (decomposition) were obtained.

Workup

  1. temperaturewas heated to the boiling point
  2. temperatureunder reflux for 16 hours or to 135°-140° C. for two hours
  3. distillationThe diluent was distilled off in vacuo
  4. dissolutionthe residue was dissolved in 30 ml of 1N NaOH
  5. filtrationthe solution was filtered
  6. filtrationThe precipitate was filtered off
  7. washwashed with water and ethanol
  8. customIt could be recrystallised from N-dimethylformamide/ethanol

Sources & evidence

ORD record
ord-126ee4a8f56c4d7d953660c171e2ab19
Source dataset
uspto-grants-1987_06
Patent number
US04670444

Reaction notes

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