2-Chloro-N,N-dimethylethylamine → HCID 57445150, compound

HRID 1893635Notes

Reaction equation

HRID 1893635 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:12])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.Cl[CH2:14][CH2:15][N:16]([CH3:18])[CH3:17].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH2:14][CH2:15][N:16]([CH3:18])[CH3:17])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 10796Cesium carbonateHCID 1357421771-chloro-2H-isoquinolin-6-one

Product 1

HCID 57445150HCID 57445150, compoundYield 120.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 1-chloro-isoquinolin-6-ol (300 mg, 1.67 mmol) in acetonitrile (16 ml) was added (2-Chloro-ethyl)-dimethyl-amine (289 mg, 2.0 mmol) and cesium carbonate (1.2 g, 3.67 mmol). The reaction was stirred at 65° C. overnight. The solvent was removed and the residue dissolved in ethyl acetate. The organic solution was washed with saturated sodium bicarbonate, dried over magnesium sulfate and concentrated. The crude product was purified using reverse phase HPLC to afford 505 mg (83%) of [2-(1-chloro-isoquinolin-6-yloxy)-ethyl]-dimethyl-amine as a white amorphous solid. LCMS found 251.04 [M+H]+.

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washThe organic solution was washed with saturated sodium bicarbonate
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe crude product was purified

Sources & evidence

ORD record
ord-5140ea610f8146359e6ea153d5aa9d3a
Source dataset
uspto-grants-2013_08
Patent number
US08513186B2

Reaction notes

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