Dimethylformamide → 6-(4-Biphenylyl)methoxy-2-[3-(N,N-dimethylamino)propyl]tetralin hydrochloride

HRID 1166535Notes

Reaction equation

HRID 1166535 reaction equation
[H-].[Na+].CN(C=O)C.[CH3:8][N:9]([CH2:11][CH2:12][CH2:13][CH:14]1[CH2:23][CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[C:19]([OH:24])[CH:20]=2)[CH2:15]1)[CH3:10].[Cl:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:29][CH:28]=1>O>[ClH:25].[C:30]1([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:29]=[CH:28][C:27]([CH2:26][O:24][C:19]2[CH:20]=[C:21]3[C:16](=[CH:17][CH:18]=2)[CH2:15][CH:14]([CH2:13][CH2:12][CH2:11][N:9]([CH3:10])[CH3:8])[CH2:23][CH2:22]3)=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 154634-Phenylbenzyl chlorideHCID 24758Sodium hydrideHCID 183615462-[3-(N,N-dimethylamino)propyl]-6-hydroxytetralin

Product 1

HCID 183615976-(4-Biphenylyl)methoxy-2-[3-(N,N-dimethylamino)propyl]tetralin hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

60% Oily sodium hydride (0.258 g) was added to a DMF solution (20 ml) of 2-[3-(N,N-dimethylamino) propyl]-6- hydroxytetralin (1.00 g) at 0° C. The reaction mixture was warmed to room temperature, and stirred for 30 minutes. This was again cooled to 0° C., and 4-(chloromethyl)biphenyl (1.04 g) as added thereto, and then stirred at room temperature for 4 hours. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, then dried, and concentrated. The residue was purified by alumina column chromatography (eluent: toluene alone to toluene/ethyl acetate=1/1), and then processed with 4 N hydrochloric acid-ethyl acetate to form a hydrochloride. The thus-formed salt was recrystallized from methanol-diisopropyl ether to obtain the entitled compound (1.30 g).

Workup

  1. temperatureThis was again cooled to 0° C.
  2. stirringstirred at room temperature for 4 hours
  3. extractionwas then extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materiala saturated aqueous sodium chloride solution, then dried
  6. concentrationconcentrated
  7. customThe residue was purified by alumina column chromatography (eluent

Sources & evidence

ORD record
ord-522be3fdb85d4e848a2bb0d01fcc1856
Source dataset
uspto-grants-2003_09
Patent number
US06613805B2

Reaction notes

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