Trifluoroacetic acid → ethyl 4-(3-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylate

HRID 39671Notes

Reaction equation

HRID 39671 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH3:35])=[CH:8][C:9](=[O:34])[N:10]2[CH2:13][CH2:14][CH2:15][C:16]2([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]2)=[CH:5][CH:4]=1.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH3:35])=[CH:8][C:9](=[O:34])[N:10]2[CH2:13][CH2:14][CH2:15][C:16]2([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 593981031-tert-butyl 4-ethyl 4-(3-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)propyl)piperidine-1,4-dicarboxylate

Product 1

HCID 59397947ethyl 4-(3-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 2 mL of a chloroform solution containing 0.45 g of 1-tert-butyl 4-ethyl 4-(3-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)propyl)piperidine-1,4-dicarboxylate, 1 mL of trifluoroacetic acid was added, and the mixture was stirred for 14 hours. The solvent was removed under reduced pressure, and water and diethyl ether were added thereto. The aqueous layer was separated, ethyl acetate was added thereto, and the resultant solution was adjusted to pH 12.5 with a 20% aqueous sodium hydroxide solution. The organic layer was separated, and the aqueous layer was extracted twice with ethyl acetate. The organic layer and the extract were combined, and the resultant solution was washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 0.29 g of a yellow oily substance, ethyl 4-(3-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylate.

Workup

  1. additionwas added
  2. customThe solvent was removed under reduced pressure, and water and diethyl ether
  3. additionwere added
  4. customThe aqueous layer was separated
  5. additionethyl acetate was added
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted twice with ethyl acetate
  8. washthe resultant solution was washed with an aqueous saturated sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-020e2e814c9f48b193b9f645bb7cd2bf
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

Loading…