Quipazine → Ethyl 2-[5-(4-quinolin-2-ylpiperazin-1-yl)pentanoylamino]cyclohex-1-enecarboxylate

HRID 1714783Notes

Reaction equation

HRID 1714783 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=1[NH:12][C:13](=[O:19])[CH2:14][CH2:15][CH2:16][CH2:17]Br)=[O:5])[CH3:2].[N:20]1([C:26]2[CH:35]=[CH:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]=2)[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=1[NH:12][C:13](=[O:19])[CH2:14][CH2:15][CH2:16][CH2:17][N:23]1[CH2:24][CH2:25][N:20]([C:26]2[CH:35]=[CH:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]=2)[CH2:21][CH2:22]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 5011QuipazineHCID 8471TriethylamineHCID 23155883Ethyl 2-(5-bromopentanoylamino)cyclohex-1-enecarboxylate

Product 1

HCID 23155633Ethyl 2-[5-(4-quinolin-2-ylpiperazin-1-yl)pentanoylamino]cyclohex-1-enecarboxylateYield 86%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 66.5 g of 2-(5-bromopentanoylamino)cyclohex-1-enecarboxylic acid ethyl ester as synthesized in above Step 7-1-C, 46.9 g of 2-piperazin-1-ylquinoline as synthesized in above Step 7-1-A, 22.3 g of triethylamine and 350 ml of toluene was heated under reflux for an overnight. The solvent was concentrated under reduced pressure, and ethyl acetate was added to the residue, followed by washing with saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over anhydrous magnesium sulfate and the solvent was concentrated under reduced pressure. The residue was purified on silica gel column chromatography (n-hexane:ethyl acetate:methanol=1:6:0.2) to provide 79.8 g (86%) of 2-[5-(4-quinolin-2-ylpiperazin-1-yl)pentanoylamino]cyclohex-1-enecarboxylic acid ethyl ester.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for an overnight
  3. concentrationThe solvent was concentrated under reduced pressure, and ethyl acetate
  4. additionwas added to the residue
  5. washby washing with saturated aqueous sodium hydrogencarbonate solution
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationthe solvent was concentrated under reduced pressure
  8. customThe residue was purified on silica gel column chromatography (n-hexane:ethyl acetate:methanol=1:6:0.2)

Sources & evidence

ORD record
ord-448e2025bf1a413c86810a34b913aef0
Source dataset
uspto-grants-2010_09
Patent number
US07799775B2

Reaction notes

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