Potassium Carbonate → HCID 16222357, compound

HRID 1435988Notes

Reaction equation

HRID 1435988 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([O:7][C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[C:14]([NH2:18])=[N:13][CH:12]=[CH:11]3)[CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][CH2:27][O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CN(C=O)C.C(#N)C>[O:28]([CH2:27][CH2:26][N:1]1[CH2:6][CH2:5][CH2:4][CH:3]([O:7][C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[C:14]([NH2:18])=[N:13][CH:12]=[CH:11]3)[CH2:2]1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 68526Benzene, (2-bromoethoxy)-HCID 688740866-(Piperidin-3-yloxy)isoquinolin-1-ylamine

Product 1

HCID 16222357HCID 16222357, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 6-(piperidin-3-yloxy)isoquinolin-1-ylamine (30 mg, 123 μmol) in DMF (1 ml) was added potassium carbonate (18 mg, 129 μmol) followed by a solution of (2-bromoethoxy)benzene (26 mg, 129 μmol) in acetonitrile (0.5 ml). The mixture was stirred for 16 h at ambient temperature, then the solvent removed in vacuo and aqueous sodium hydrogen carbonate added. The mixture was extracted with chloroform/iso-propanol (3:1), dried (magnesium sulphate) and concentrated in vacuo to give a residue. The residue was purified by prep-HPLC to give 6-[1-(2-phenoxyethyl)piperidin-3-yloxy]-isoquinolin-1-ylamine (12.5 mg) El-MS: m/z=364.8 [M+H]+.

Workup

  1. customthe solvent removed in vacuo and aqueous sodium hydrogen carbonate
  2. additionadded
  3. extractionThe mixture was extracted with chloroform/iso-propanol (3:1)
  4. dry with materialdried (magnesium sulphate)
  5. concentrationconcentrated in vacuo
  6. customto give a residue
  7. customThe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-509d53a7fe784278934e4039343f54d1
Source dataset
uspto-grants-2009_11
Patent number
US07618985B2

Reaction notes

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