Potassium Carbonate → HCID 67465008, compound

HRID 1522838Notes

Reaction equation

HRID 1522838 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([OH:13])=[N:8][CH:7]=[CH:6]2.C([O-])([O-])=O.[K+].[K+].Cl.Cl[CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>CC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([O:13][CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)=[N:8][CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 178487746HCID 178487746, compound

Product 1

HCID 67465008HCID 67465008, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 6-methoxyisoquinoline-1-ol (1.00 g, 5.71 mmol) in acetone, K2CO3 (4.73 g, 34.26 mmol) and N-chloroethyl-piperidine hydrochloride salt (1.37 g, 7.42 mmol) were added. The solution was heated to reflux for 6 hours. The solution was evaporated to dryness. The residue was hydrolyzed by adding water, then extracted with ethyl acetate. The organic layers were separated and dried over anhydrous MgSO4. The solvent was removed under reduced pressure. The residue was purified by flash chromatography (silica-gel; methylene chloride/methanol=9/1 v/v) to give a yellow oil product, 1.50 g, 92.0% yield. MS: 287.2 [M+H]+. 1H NMR (DMSO-d6, 300 MHz) δ 8.11 (d, 1H, J=9.0 Hz), 7.39 (d, 1H, J=7.5 Hz), 7.10-7.13 (m, 2H), 6.51 (d, 1H, J=7.5 Hz), 4.02 (t, 2H, J=6.6 Hz), 3.86 (s, 3H), 2.55 (t, 2H, J=6.5 Hz), 2.41 (br, 4H), 1.52-1.44 (m, 4H), 1.37-114 (m, 2H).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 6 hours
  3. customThe solution was evaporated to dryness
  4. additionby adding water
  5. extractionextracted with ethyl acetate
  6. customThe organic layers were separated
  7. dry with materialdried over anhydrous MgSO4
  8. customThe solvent was removed under reduced pressure
  9. customThe residue was purified by flash chromatography (silica-gel; methylene chloride/methanol=9/1 v/v)
  10. customto give a yellow oil product, 1.50 g, 92.0% yield

Sources & evidence

ORD record
ord-0040c1ca9baf4b7bbb608ef5631cf000
Source dataset
uspto-grants-2015_07
Patent number
US09078888B2

Reaction notes

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