Potassium Carbonate → 6-(5-Phenyl-1,3,4-oxadiazol-2-yl)methoxy-2-piperidinomethyltetralin hydrochloride

HRID 1166546Notes

Reaction equation

HRID 1166546 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][CH:7]([CH2:12][N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[CH2:6][CH2:5]2.[Cl:19][CH2:20][C:21]1[O:22][C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:24][N:25]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[ClH:19].[C:26]1([C:23]2[O:22][C:21]([CH2:20][O:1][C:2]3[CH:3]=[C:4]4[C:9](=[CH:10][CH:11]=3)[CH2:8][CH:7]([CH2:12][N:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[CH2:6][CH2:5]4)=[N:25][N:24]=2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 3149412-(Chloromethyl)-5-phenyl-1,3,4-oxadiazoleHCID 219398616-Hydroxy-2-piperidinomethyltetralin

Product 1

HCID 229985536-(5-Phenyl-1,3,4-oxadiazol-2-yl)methoxy-2-piperidinomethyltetralin hydrochlorideYield 69.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-hydroxy-2-piperidinomethyltetralin (141 mg, free form of Reference Example 19) and 2-chloromethyl-5-phenyl-1,3,4-oxadiazole (148 mg) in DMF (3 ml) was added potassium carbonate (143 mg) and the reaction mixture was stirred at room temperature for 24 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 silica gel column chromatography (eluent: ethyl acetate: methanol=10:1) and alumina column chromatography (eluent:ethyl acetate: hexane=1:4), and then converted into its hydrochloride, which was further recrystallized from methanol-diethyl ether to obtain the titled compound (175 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 silica gel column chromatography (eluent: ethyl acetate: methanol=10:1) and alumina column chromatography (eluent:ethyl acetate: hexane=1:4)
  6. customwas further recrystallized from methanol-diethyl ether

Sources & evidence

ORD record
ord-b052644c32754254b323cd18657f9d00
Source dataset
uspto-grants-2003_09
Patent number
US06613805B2

Reaction notes

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