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

HRID 1890731

반응식

HRID 1890731 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-af0443489ea74fdda2af49b22b005c94
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507491B2

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