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

HRID 1766016노트

반응식

HRID 1766016 반응식
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

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 825094-Phenylpiperidinium chloride

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-f44d78c70c484ad3b42172a877467ff6
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07229986B2

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