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

HRID 854040

반응식

HRID 854040 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 702Ethanol용매HCID 1140Toluene용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-bf4405f3807a4f0686ddbaae540eb835
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07256204B2

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