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

HRID 382969ノート

反応式

HRID 382969 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d4d3691af1224d3facddd128890a74bb
出典データセット
uspto-grants-2001_10
特許番号
US06310107B1

反応ノート

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