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

HRID 19536Notes

Reaction equation

HRID 19536 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-carboxylic acid ethyl ester (1.1 g, 2.96 mmol) obtained in Step 5 was dissolved in N,N-dimethyl formamide. Pyridine (264 μl, 3.26 mmol) and morpholine (284 μl, 3.26 mmol) were added thereto, followed by stirring for 2 hrs. Upon the completion of the reaction, the resulting mixture washed successively with saturated ammonium chloride and saline and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous MgSO4 and concentrated under a reduced pressure. The resulting residue was purified by flash chromatography to obtain 180 mg of the titled compound (yield: 16.1%) in red oil state.

Workup

  1. customUpon the completion of the reaction
  2. washthe resulting mixture washed successively with saturated ammonium chloride and saline
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated under a reduced pressure
  7. customThe resulting residue was purified by flash chromatography

Sources & evidence

ORD record
ord-3abde345c04a418790cbecc6d4b73253
Source dataset
uspto-grants-2010_06
Patent number
US07745439B2

Reaction notes

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