1-(2-Hydroxyethyl)piperazine → HCID 53908075, compound

HRID 894822Notes

Reaction equation

HRID 894822 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:25])[N:8](C)[C:9]2[C:14]([C:15]=1[N:16]1[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]1)=[CH:13][C:12]([Cl:23])=[CH:11][CH:10]=2)=[O:5])[CH3:2].[C:26](=O)([O-])[O-:27].[Na+].[Na+].OCCN1CCNCC1>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:25])[NH:8][C:9]2[C:14]([C:15]=1[N:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH2:26][OH:27])[CH2:18][CH2:17]1)=[CH:13][C:12]([Cl:23])=[CH:11][CH:10]=2)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 76771-(2-Hydroxyethyl)piperazineHCID 10340Sodium CarbonateHCID 12769801HCID 12769801, compound

Product 1

HCID 53908075HCID 53908075, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 6.09 g. of 4,6-dichloro-1,2-dihydro-1-methyl-2-oxo-3-quinolinecarboxylic acid ethyl ester (prepared as in Example 4), 2.12 g. of sodium carbonate, and 2.6 g. of N-2-hydroxyethylpiperazine in 50 ml. of ethanol was heated under reflux for 3 hours. The reaction mixture was filtered under suction and the filtrate taken to dryness in a rotary evaporator. On triturating the residual oil with diethyl ether gave 6.0 g. of product, m.p. 130°-134° C. Recrystallization from ethyl acetate gave 4.4 g. of the title compound, m.p. 135°-138° C.

Workup

  1. additionA stirred mixture of 6.09 g
  2. temperatureunder reflux for 3 hours
  3. filtrationThe reaction mixture was filtered under suction
  4. customthe filtrate taken to dryness in a rotary evaporator
  5. customOn triturating the residual oil with diethyl ether
  6. customgave 6.0 g
  7. customRecrystallization from ethyl acetate
  8. customgave 4.4 g

Sources & evidence

ORD record
ord-3bec8f65b1814697819226eeae40c04b
Source dataset
uspto-grants-1981_08
Patent number
US04284768

Reaction notes

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