Potassium Carbonate → 2-(N,N-Dimethylamino)methyl-6-(2-quinolyl)methoxytetralin dihydrochloride

HRID 1166544Notes

Reaction equation

HRID 1166544 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].[ClH:16].[Cl:17][CH2:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[ClH:17].[ClH:16].[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][CH2:18][C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]=3)[CH:11]=2)[CH2:6]1)[CH3:1]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 219397642-(N,N-Dimethylamino)methyl-6-hydroxytetralin

Product 1

HCID 183615572-(N,N-Dimethylamino)methyl-6-(2-quinolyl)methoxytetralin dihydrochloride

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(N,N-dimethylamino)methyl-6-hydroxytetralin (153 mg, a free form of Reference Example 16) and 2-chloromethylquinoline hydrochloride (189 mg) in DMF (5 ml) was added potassium carbonate (260 mg) and the reaction mixture was stirred at room temperature for 26 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) and then converted into its dihydrochloride, which was further recrystallized from methanol-ethyl acetate to obtain the titled compound (191 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)
  6. customwas further recrystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-8006c0c4cd5b4a4bbad7d616a72c4edb
Source dataset
uspto-grants-2003_09
Patent number
US06613805B2

Reaction notes

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