Piperazine → HCID 12818649, compound

HRID 2285833Notes

Reaction equation

HRID 2285833 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:24])[N:8]([CH2:22][CH3:23])[C:9]2[C:14]([C:15]=1[N:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1)=[CH:13][CH:12]=[C:11]([CH3:21])[N:10]=2)=[O:5])[CH3:2].[NH:25]1CCNCC1>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:24])[N:8]([CH2:22][CH3:23])[C:9]2[C:14]([C:15]=1[N:16]1[CH2:20][CH2:19][NH:25][CH2:18][CH2:17]1)=[CH:13][CH:12]=[C:11]([CH3:21])[N:10]=2)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 12818639HCID 12818639, compound

Product 1

HCID 12818649HCID 12818649, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 1.47 g. (0.005 mole) of 1-ethyl-1,2-dihydro-4-chloro-7-methyl-2-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester (Example 30) and 1.72 g. (0.02 mole) of piperazine in 20 ml. of ethanol was heated under reflux for 5 hours. The mixture was filtered and the filtrate was diluted with 100 ml. of water and was extracted with 50 ml. of diethyl ether. The ether layer was dried over magnesium sulfate, filtered and was evaporated in an evaporating dish at room temperature. The residue was recrystallized from heptane to give 0.3 g. of product, m.p. 137°-139° C.

Workup

  1. additionA stirred mixture of 1.47 g
  2. temperatureunder reflux for 5 hours
  3. filtrationThe mixture was filtered
  4. additionthe filtrate was diluted with 100 ml
  5. extractionof water and was extracted with 50 ml
  6. dry with materialThe ether layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. customwas evaporated in an evaporating dish at room temperature
  9. customThe residue was recrystallized from heptane
  10. customto give 0.3 g

Sources & evidence

ORD record
ord-40a9f340541147b9bcaf9e5464cc0618
Source dataset
uspto-grants-1982_04
Patent number
US04324893

Reaction notes

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