Pyridine → 6-morpholine-4-ylmethyl-1-oxo-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

HRID 17895Notes

Reaction equation

HRID 17895 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:23])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([CH2:21]Br)[CH:9]=2)=[O:5])[CH3:2].N1C=CC=CC=1.[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:23])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([CH2:21][N:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1)[CH:9]=2)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8083MorpholineHCID 686975466-bromomethyl-1-oxo-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

Product 1

HCID 686940766-morpholine-4-ylmethyl-1-oxo-3-phenyl-1H-indene-2-carboxylic acid ethyl esterYield 16.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Bromomethyl-1-oxo-3-phenyl-1H-indene-2-carboxylate ethyl ester (1.1 g, 2.96 mmol) was dissolved in N,N-dimethylformamide. Pyridine (264 μl, 3.26 mmol) and morpholine (284 μl, 3.26 mmol) were added thereto and the mixture was stirred for 2 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate/ammonium chloride/saturated sodium chloride, dried over anhydrous magnesium sulfate, concentrated, and the resulting residue was purified by column chromatography to obtain 180 mg of 6-(morpholine-4-yl methyl)-1-oxo-3-phenyl-1H-indene-2-carboxylate ethyl ester (180 mg, yield 16.1%) as red oil.

Workup

  1. extractionthe organic layer was extracted with ethyl acetate/ammonium chloride/saturated sodium chloride
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customthe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-5588cf0282924f31b7a6d15cfc6a3e09
Source dataset
uspto-grants-2010_06
Patent number
US07741323B2

Reaction notes

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