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

HRID 1766016ノート

反応式

HRID 1766016 の反応式
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

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 825094-Phenylpiperidinium chloride

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-f44d78c70c484ad3b42172a877467ff6
出典データセット
uspto-grants-2007_06
特許番号
US07229986B2

反応ノート

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