Hydrochloric Acid → 7-(4-Biphenylyl)methoxy-3-(N,N-dimethylamino) methyl-1,2,3,4-tetrahydroquinoline hydrochloride

HRID 382984ノート

反応式

HRID 382984 の反応式
[CH3:1][N:2]([CH2:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][C:10]([OH:15])=[CH:11][CH:12]=2)[NH:7][CH2:6]1)[CH3:3].[C:16]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:21]=[CH:20][C:19]([CH2:22]O)=[CH:18][CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[ClH:61]>C1COCC1>[ClH:61].[C:16]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:17]=[CH:18][C:19]([CH2:22][O:15][C:10]2[CH:9]=[C:8]3[C:13]([CH2:14][CH:5]([CH2:4][N:2]([CH3:1])[CH3:3])[CH2:6][NH:7]3)=[CH:12][CH:11]=2)=[CH:20][CH:21]=1

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 19186(1,1'-Biphenyl)-4-methanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 219397443-(Dimethylamino)methyl-1,2,3,4-tetrahydro-7-quinolinol

生成物 1

HCID 183615217-(4-Biphenylyl)methoxy-3-(N,N-dimethylamino) methyl-1,2,3,4-tetrahydroquinoline hydrochloride

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 3-(dimethylamino)methyl-1,2,3,4-tetrahydro-7-quinolinol (344 mg), 4-biphenylylmethanol (368 mg), and triphenylphosphine (525 mg) in THF (20 ml) was added diethyl azodicarboxylate (348 mg). After stirring at room temperature for one hr, the reaction mixture was poured into 1 N aqueous hydrochloric acid and washed with ethyl acetate. The water layer was neutralized by 1 N aqueous sodium hydroxide, diluted with saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried, and concentrated. The residue was purified by alumina column chromatography (eluent: ethyl acetate:hexane=1:4) and converted into its hydrochloride, which was further recrystallized from ethanol-diisopropyl ether to obtain the titled compound (214 mg).

後処理

  1. washwashed with ethyl acetate
  2. additiondiluted with saturated aqueous sodium bicarbonate
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium chloride
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by alumina column chromatography (eluent: ethyl acetate:hexane=1:4)
  8. customwas further recrystallized from ethanol-diisopropyl ether

出典と根拠

ORDレコード
ord-859d018afccc495aa65b45b2f07dc458
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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