Hydrochloric Acid → HCID 18361487, compound

HRID 1166550Notes

Reaction equation

HRID 1166550 reaction equation
[CH2:1]([N:3]([CH2:6][CH2:7][CH:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([OH:18])[CH:14]=2)[CH2:9]1)[CH2:4][CH3:5])[CH3:2].[H-].[Na+].[Cl:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:25][CH:24]=1.Cl.C(=O)(O)[O-].[Na+]>CN(C=O)C.O>[ClH:21].[C:26]1([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:25]=[CH:24][C:23]([CH2:22][O:18][C:13]2[CH:14]=[C:15]3[C:10](=[CH:11][CH:12]=2)[CH2:9][CH:8]([CH2:7][CH2:6][N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[CH2:17][CH2:16]3)=[CH:28][CH:27]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 154634-Phenylbenzyl chlorideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 22998631HCID 22998631, compound

Product 1

HCID 18361487HCID 18361487, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of (+)-2-[2-(N,N-diethylamino) ethyl]-6-hydroxytetralin (4.5 g) in DMF (60 ml) was added sodium hydride (60% in oil, 1.46 g) at 0° C. The reaction mixture was stirred at room temperature for 30 min and a solution of 4-chloromethylbiphenyl (4.08 g) in DMF (40 ml) was added. After stirring at room temperature for 2 hr, the reaction mixture was poured into water, neutralized with 1 N aqueous hydrochloric acid. Saturated aqueous sodium bicarbonate (50 ml) was added and the reaction mixture was extracted with combined solvent of ethyl acetate and THF (1:1). The organic layer was dried and concentrated. The residue was purified by silica gel column chromatography (eluent: ethyl acetate to ethyl acetate: triethylamine=4:1) and converted into its hydrochloride, which was recrystallized from ethanol-diisopropyl ether to obtain the titled compound (6 g).

Workup

  1. stirringAfter stirring at room temperature for 2 hr
  2. extractionthe reaction mixture was extracted with combined solvent of ethyl acetate and THF (1:1)
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate to ethyl acetate: triethylamine=4:1)
  6. customwas recrystallized from ethanol-diisopropyl ether

Sources & evidence

ORD record
ord-861fc5d644a142879f21452036dee518
Source dataset
uspto-grants-2003_09
Patent number
US06613805B2

Reaction notes

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