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

HRID 1714771Notes

Reaction equation

HRID 1714771 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([NH:8][C:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:7].[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>[N:27]1[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:34]=[CH:35][C:26]=1[N:20]1[CH2:25][CH2:24][N:23]([CH2:2][CH2:3][CH2:4][CH2:5][C:6]([NH:8][C:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:7])[CH2:22][CH2:21]1

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

In 350 ml of toluene, 66.5 g of ethyl 2-(5-bromopentanoylamino)cyclohex-1-enecarboxylate as synthesized in above Step 4-1-B, 46.9 g of 2-piperazin-1-ylquinoline and 22.3 g of triethylamine were dissolved and heated under reflux for an overnight. The solvent was distilled off 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 from which the solvent was distilled off under reduced pressure. Purifying the residue on silica gel column chromatography (n-hexane:ethyl acetate:methanol=1:6:0.2) to provide 79.8 g (86%) of ethyl 2-[5-(4-quinolin-2-ylpiperazin-1-yl)pentanoylamino]cyclohex-1-enecarboxylate.

Workup

  1. dissolutionwere dissolved
  2. temperatureheated
  3. temperatureunder reflux for an overnight
  4. distillationThe solvent was distilled off under reduced pressure, and ethyl acetate
  5. additionwas added to the residue
  6. washby washing with saturated aqueous sodium hydrogencarbonate solution
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. distillationfrom which the solvent was distilled off under reduced pressure
  9. customPurifying the residue on silica gel column chromatography (n-hexane:ethyl acetate:methanol=1:6:0.2)

Sources & evidence

ORD record
ord-390e2549fd5a471fbfe81cbd08d9a018
Source dataset
uspto-grants-2010_09
Patent number
US07799775B2

Reaction notes

Loading…