Phosphorus trichloride → Ethyl 2-[5-(4-quinolin-2-ylpiperazin-1-yl)hexanoylamino]cyclohex-1-enecarboxylate

HRID 1714788Notes

Reaction equation

HRID 1714788 reaction equation
[NH2:1][C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].P(Cl)(Cl)Cl.[N:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1[N:27]1[CH2:32][CH2:31][N:30]([CH:33]([CH3:40])[CH2:34][CH2:35][CH2:36][C:37](O)=[O:38])[CH2:29][CH2:28]1>N1C=CC=CC=1>[N:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1[N:27]1[CH2:28][CH2:29][N:30]([CH:33]([CH3:40])[CH2:34][CH2:35][CH2:36][C:37]([NH:1][C:2]2[CH2:7][CH2:6][CH2:5][CH2:4][C:3]=2[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:38])[CH2:31][CH2:32]1

Participants

5

Reactant 3

HCID 24387Phosphorus trichlorideHCID 312929Ethyl 2-aminocyclohex-1-ene-1-carboxylateHCID 231559185-(4-Quinoline-2-ylpiperazin-1-yl)hexanoic acid

Product 1

HCID 23155828Ethyl 2-[5-(4-quinolin-2-ylpiperazin-1-yl)hexanoylamino]cyclohex-1-enecarboxylateYield 38.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 170 mg of ethyl 2-aminocyclohex-1-enecarboxylate as synthesized in Step 7-1-B in 5 ml of pyridine, 70 mg of phosphorus trichloride was added under cooling with ice, followed by 15 minutes' stirring. Raising the temperature to room temperature, 327 mg of 5-(4-quinoline-2-ylpiperazin-1-yl)hexanoic acid as synthesized in above Step 7-14-C was added to the solution and stirred for 3 hours. Distilling the pyridine off under reduced pressure, the residue was extracted with ethyl acetate and washed with water. 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 (ethyl acetate) to provide 182 mg (38%) of ethyl 2-[5-(4-quinolin-2-ylpiperazin-1-yl)hexanoylamino]cyclohex-1-enecarboxylate.

Workup

  1. temperatureunder cooling with ice
  2. additionwas added to the solution
  3. stirringstirred for 3 hours
  4. distillationDistilling the pyridine off under reduced pressure
  5. extractionthe residue was extracted with ethyl acetate
  6. washwashed with water
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. concentrationthe solvent was concentrated under reduced pressure
  9. customThe residue was purified on silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-6a77593a7b5c477a9a546085ff9cac5b
Source dataset
uspto-grants-2010_09
Patent number
US07799775B2

Reaction notes

Loading…