Potassium Carbonate → HCID 9866341, compound

HRID 1356448Notes

Reaction equation

HRID 1356448 reaction equation
[ClH:1].[CH2:2]([N:5]([CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)[CH2:6][CH2:7][CH3:8])[CH2:3][CH3:4].Br[CH2:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=1.C(=O)([O-])[O-].[K+].[K+].[H-].[Na+]>O.CN(C=O)C>[ClH:1].[CH:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:29]=[CH:30][C:21]=1[CH2:20][O:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][CH2:10][CH2:9][N:5]([CH2:6][CH2:7][CH3:8])[CH2:2][CH2:3][CH3:4])=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 703202-BromomethylnaphthaleneHCID 18508345HCID 18508345, compound

Product 1

HCID 9866341HCID 9866341, compoundYield 73.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-[3-(N,N-dipropylamino)propyl]phenol hydrochloride (0.152 g), 2-bromomethylnaphthalene (0.165 g), and DMF (10 ml) was added potassium carbonate (0.131 g). Sodium hydride (60% oil dispersion: 0.044 g) was added to the reaction mixture under ice cooling and the reaction mixture was stirred at room temperature for one 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 sequentially, dried, and concentrated. The residue was purified by alumina column chromatography (eluent: hexane/ethyl acetate=4/1) and converted into its hydrochloride by 4 N hydrochloric acid/ethyl acetate solution followed by recrystallization from methanol/diisopropylether to obtain the titled compound (0.169 g).

Workup

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

Sources & evidence

ORD record
ord-e0be06b40494431db53b4e65b0ab9225
Source dataset
uspto-grants-2003_07
Patent number
US06586475B1

Reaction notes

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