Potassium Carbonate → 2-(N,N-Dimethylamino)methyl-6-(5-phenyl-1,3,4-oxadiazol-2-yl)methoxytetralin

HRID 1166545Notes

Reaction equation

HRID 1166545 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:15])[CH:11]=2)[CH2:6]1)[CH3:3].Cl[CH2:17][C:18]1[O:19][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:21][N:22]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH3:3][N:2]([CH2:4][CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH2:17][C:18]3[O:19][C:20]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)=[N:21][N:22]=3)[CH:11]=2)[CH2:6]1)[CH3:1]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 3149412-(Chloromethyl)-5-phenyl-1,3,4-oxadiazoleHCID 219397642-(N,N-Dimethylamino)methyl-6-hydroxytetralin

Product 1

HCID 183615712-(N,N-Dimethylamino)methyl-6-(5-phenyl-1,3,4-oxadiazol-2-yl)methoxytetralin

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(N,N-dimethylamino)methyl-6-hydroxytetralin (206 mg, a free form of Reference Example 16) and 2-chloromethyl-5-phenyl-1,3,4-oxadiazole (231 mg) in DMF (5 ml) was added potassium carbonate (215 mg) and the reaction mixture was stirred at room temperature for 15 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, dried, and concentrated. The residue was purified by alumina column chromatography (eluent: ethyl acetate: hexane=1:2) to obtain the titled compound (307 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by alumina column chromatography (eluent: ethyl acetate: hexane=1:2)

Sources & evidence

ORD record
ord-cb5ce783f866422e87acd7eb327169d6
Source dataset
uspto-grants-2003_09
Patent number
US06613805B2

Reaction notes

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