Acetic Acid → Quinoline, 2-(2-(4-phenyl-1-piperazinyl)ethyl)-

HRID 1576769Notes

Reaction equation

HRID 1576769 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)=[CH2:2].C(O)(=O)C.[C:17]1([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(O)C>[C:17]1([N:23]2[CH2:28][CH2:27][N:26]([CH2:2][CH2:1][C:3]3[CH:12]=[CH:11][C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[N:4]=3)[CH2:25][CH2:24]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 70961-PhenylpiperazineHCID 698752-Vinylquinoline

Product 1

HCID 3044971Quinoline, 2-(2-(4-phenyl-1-piperazinyl)ethyl)-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 2-vinylquinoline (0.1 mole, 15g.) and glacial acetic acid (0.1 mole, 6 g.) in ethanol (95%, 100 ml.) N-phenylpiperazine (0.1 mole) was added and the solution was refluxed for 15 hrs. The solvent was removed and the remaining oil was heated in vacuo (1 mm. Hg) to 100°C. The oil left in the flask crystallized out on cooling and was recrystallized from ether-petroleum ether to give the titular product m.p. 79°C.

Workup

  1. additionwas added
  2. temperaturethe solution was refluxed for 15 hrs
  3. customThe solvent was removed
  4. waitThe oil left in the flask
  5. customcrystallized out
  6. temperatureon cooling
  7. customwas recrystallized from ether-petroleum ether

Sources & evidence

ORD record
ord-a1faf3f098a3419e96386523662d1204
Source dataset
uspto-grants-1976_09
Patent number
US03983121

Reaction notes

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