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

HRID 854041노트

반응식

HRID 854041 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-08e00ad54bdd43bd9405a9b842802c44
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07256204B2

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