Hydrochloric Acid → HCID 12818634, compound

HRID 2285819Notes

Reaction equation

HRID 2285819 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:19])[N:8]([CH2:17][CH3:18])[C:9]2[C:14]([C:15]=1Cl)=[CH:13][CH:12]=[CH:11][N:10]=2)=[O:5])[CH3:2].[CH3:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C(=O)([O-])[O-].[Na+].[Na+].Cl>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:19])[N:8]([CH2:17][CH3:18])[C:9]2[C:14]([C:15]=1[N:24]1[CH2:25][CH2:26][N:21]([CH3:20])[CH2:22][CH2:23]1)=[CH:13][CH:12]=[CH:11][N:10]=2)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 531671-MethylpiperazineHCID 13952728HCID 13952728, compound

Product 1

HCID 12818634HCID 12818634, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 4.2 g. (0.015 mole) of 1-ethyl-1,2-dihydro-4-chloro-2-oxo-1,8-naphthridine-3-carboxylic acid ethyl ester (prepared in the manner described in Example 30), 1.5 g. (0.015 mole) of N-methylpiperazine and 1.6 g. (0.015 mole) of sodium carbonate in 20 ml. of ethanol was heated under reflux for 5 hours. The mixture was filtered and the filtrate was evaporated in a rotary evaporator. The residue was triturated with 50 ml. of 20% aqueous sodium carbonate and this mixture was extracted with 50 ml. of diethyl ether. The ether layer was dried over magnesium sulfate, filtered and was diluted with 50 ml. of ethanol. This solution was slowly acidified with an ethereal hydrochloric acid solution. The precipitate which formed was collected and was recrystallized from ethanol to give 2.5 g. of product as the hydrochloride, m.p. 230°-233° C.

Workup

  1. additionA stirred mixture of 4.2 g
  2. temperatureunder reflux for 5 hours
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated in a rotary evaporator
  5. customThe residue was triturated with 50 ml
  6. extractionof 20% aqueous sodium carbonate and this mixture was extracted with 50 ml
  7. dry with materialThe ether layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. additionwas diluted with 50 ml
  10. customThe precipitate which formed
  11. customwas collected
  12. customwas recrystallized from ethanol
  13. customto give 2.5 g

Sources & evidence

ORD record
ord-ef7d710f35014a1389a3867a34bd840e
Source dataset
uspto-grants-1982_04
Patent number
US04324893

Reaction notes

Loading…