Ethyl Acetate → 1-[(4-Phenyl-1-piperidinyl)carbonyl]-1,2,3,4-tetrahydroquinoline

HRID 1766016Notes

Reaction equation

HRID 1766016 reaction equation
Cl.[C:2]1([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:14].[Na+].C(O[CH2:20][CH3:21])(=O)C>CS(C)=O>[C:2]1([CH:8]2[CH2:9][CH2:10][N:11]([C:12]([N:11]3[C:20]4[C:21](=[CH:7][CH:2]=[CH:3][CH:4]=4)[CH2:8][CH2:9][CH2:10]3)=[O:14])[CH2:12][CH2:13]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 825094-Phenylpiperidinium chloride

Product 1

HCID 178488691-[(4-Phenyl-1-piperidinyl)carbonyl]-1,2,3,4-tetrahydroquinoline

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-Nitrophenyl 3,4-dihydroquinoline-1(2H)-carboxylate obtained in 1) above was dissolved in DMSO (10 ml), and 4-phenylpiperidine hydrochloride (1.58 g, 7.97 mmol) and 4 N aqueous sodium hydroxide (2.09 ml, 8.36 mmol) were added thereto and stirred at room temperature for 22.5 hours. 60 ml ethyl acetate was added to the reaction solution which was then washed with an aqueous potassium carbonate solution and a saturated saline solution. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure, and the resultant residues were purified by silica gel column chromatography (developing solvent; hexane:ethyl acetate=2:1), whereby 2.10 g of the title compound was obtained as pale yellow liquid.

Workup

  1. washwas then washed with an aqueous potassium carbonate solution
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customthe resultant residues were purified by silica gel column chromatography (developing solvent; hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-f44d78c70c484ad3b42172a877467ff6
Source dataset
uspto-grants-2007_06
Patent number
US07229986B2

Reaction notes

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