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

HRID 1890731

Reaction equation

HRID 1890731 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-af0443489ea74fdda2af49b22b005c94
Source dataset
uspto-grants-2013_08
Patent number
US08507491B2

Linked notes

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