Sodium Chloride → 6-(3'-Aminobiphenyl-4-yl)methoxy-2-[2-(N,N-dimethylamino)ethyl]tetralin hydrochloride

HRID 854040

反応式

HRID 854040 の反応式
[NH2:1][C:2]1[CH:3]=[C:4](OB(O)O)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].Br[C:19]1[CH:41]=[CH:40][C:22]([CH2:23][O:24][C:25]2[CH:26]=[C:27]3[C:32](=[CH:33][CH:34]=2)[CH2:31][CH:30]([CH2:35][CH2:36][N:37]([CH3:39])[CH3:38])[CH2:29][CH2:28]3)=[CH:21][CH:20]=1.[Cl-:42].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.C(O)C>[ClH:42].[NH2:1][C:2]1[CH:7]=[C:6]([C:19]2[CH:41]=[CH:40][C:22]([CH2:23][O:24][C:25]3[CH:26]=[C:27]4[C:32](=[CH:33][CH:34]=3)[CH2:31][CH:30]([CH2:35][CH2:36][N:37]([CH3:39])[CH3:38])[CH2:29][CH2:28]4)=[CH:21][CH:20]=2)[CH:5]=[CH:4][CH:3]=1

参加物

8

反応物 4

HCID 5234Sodium ChlorideHCID 10340Sodium CarbonateHCID 183614846-(4-bromobenzyl)oxy-2-[2-(N,N-dimethylamino)ethyl]tetralinHCID 218958363-Aminophenylboric acid

生成物 1

HCID 183615236-(3'-Aminobiphenyl-4-yl)methoxy-2-[2-(N,N-dimethylamino)ethyl]tetralin hydrochloride

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒

実験手順

An ethanol solution (10 ml) of 3-aminophenylboric acid (1.3 g) and an aqueous 2M sodium carbonate solution (10 ml) were added to a toluene solution (80 ml) of 6-(4-bromobenzyl)oxy-2-[2-(N,N-dimethylamino)ethyl]tetralin (3.00 g) and tetrakis(triphenylphosphine) palladium (0.45 g). The reaction mixture was heated under reflux for 12 hours in an argon atmosphere. A saturated aqueous sodium chloride solution was added to this, which was then extracted with ethyl acetate. The organic layer was dried, and then concentrated. The residue was purified by alumina column chromatography (eluent:ethyl acetate/hexane=1/2), 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 (0.78 g).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 12 hours in an argon atmosphere
  3. extractionwas then extracted with ethyl acetate
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customThe residue was purified by alumina column chromatography (eluent:ethyl acetate/hexane=1/2)

出典と根拠

ORDレコード
ord-bf4405f3807a4f0686ddbaae540eb835
出典データセット
uspto-grants-2007_08
特許番号
US07256204B2

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