Formaldehyde → 3-methyl-4-(piperidin-1-yl)methyl-2H-isoquinolin-1-one

HRID 1783309Notes

Reaction equation

HRID 1783309 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:7]=O.[CH3:9][C:10]1[NH:11][C:12](=[O:20])[C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2>C(O)(=O)C>[CH3:9][C:10]1[NH:11][C:12](=[O:20])[C:13]2[C:18]([C:19]=1[CH2:7][N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[CH:17][CH:16]=[CH:15][CH:14]=2

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8082PiperidineHCID 32444773-Methyl-1,2-dihydroisoquinolin-1-one

Product 1

HCID 230847193-methyl-4-(piperidin-1-yl)methyl-2H-isoquinolin-1-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

Piperidine (0.747 mL) and paraformaldehyde (271 mg) were dissolved in acetic acid (3 mL), and the mixture was stirred at 70° C. for 5 min. 3-Methyl-2H-isoquinolin-1-one (302 mg) was added to the reaction mixture, and the mixture was heated under reflux for 2.5 hrs. After the completion of the reaction, the reaction mixture was concentrated, aqueous potassium carbonate solution was added. The mixture was extracted with chloroform, and the organic layer was dried over magnesium sulfate. The solvent was evaporated, and the obtained residue was purified by silica gel column chromatography (chloroform:methanol=20:1) to give 3-methyl-4-(piperidin-1-yl)methyl-2H-isoquinolin-1-one (99.3 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2.5 hrs
  3. customAfter the completion of the reaction
  4. concentrationthe reaction mixture was concentrated
  5. additionaqueous potassium carbonate solution was added
  6. extractionThe mixture was extracted with chloroform
  7. dry with materialthe organic layer was dried over magnesium sulfate
  8. customThe solvent was evaporated
  9. customthe obtained residue was purified by silica gel column chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-86a30e2990794aef9bb19dd83a50b9d6
Source dataset
uspto-grants-2009_03
Patent number
US07501412B2

Reaction notes

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