Water → 1-(5-Bromo-3,4-dihydroisoquinolin-2(1H)-yl)propan-2-one

HRID 1505043

反応式

HRID 1505043 の反応式
Cl.[Br:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][NH:7][CH2:8]2.Cl[CH2:14][C:15](=[O:17])[CH3:16].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C(OCC)(=O)C>[Br:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][N:7]([CH2:14][C:15](=[O:17])[CH3:16])[CH2:8]2

参加物

7

反応物 4

HCID 962WaterHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 450740035-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride

生成物 1

HCID 583180431-(5-Bromo-3,4-dihydroisoquinolin-2(1H)-yl)propan-2-one

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture containing 5-bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride (1 g, 4 mmol), chloroacetone (407 mg, 4.4 mmol) and potassium carbonate (1.38 g, 10 mmol) in dimethyl formamide (DMF) (8 ml) is stirred at room temperature for 18 hours. To this mixture is added water (50 ml) and ethyl acetate (50 ml). The organic layer is separated, washed with brine, dried over MgSO4, and concentrated. The crude product is purified by flash column chromatography using 30% ethyl acetate in dichloromethane as eluent to give 1-(5-Bromo-3,4-dihydroisoquinolin-2(1H)-yl)propan-2-one as an orange oil. LC-MS m/z: 269.1 (M+1).

後処理

  1. customThe organic layer is separated
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product is purified by flash column chromatography

出典と根拠

ORDレコード
ord-fa029e8b621649dc8a8aca503df3aa64
出典データセット
uspto-grants-2015_12
特許番号
US09216964B2

関連ノート

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