Hydrochloric Acid → 4-(1-methylpiperidin-4-yl)-2H-isoquinolin-1-one

HRID 1783308Notes

Reaction equation

HRID 1783308 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[NH:10][CH:9]=2)[CH2:4][CH2:3]1.C=O.[C:21](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl>C(#N)C>[CH3:21][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[NH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 23084775HCID 23084775, compound

Product 1

HCID 102434554-(1-methylpiperidin-4-yl)-2H-isoquinolin-1-oneYield 19.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-(Piperidin-4-yl)-2H-isoquinolin-1-one hydrochloride (0.5 g) obtained in Example 31 and 35% aqueous formalin solution (0.33 g) were dissolved in acetonitrile (20 mL), and sodium triacetoxyborohydride (0.81 g) was added under ice-cooling, and the mixture was stirred at room temperature for 3 hrs. After the completion of the reaction, diluted hydrochloric acid was added to the reaction mixture. The mixture was once heated under reflux, and the solvent was evaporated. Aqueous potassium carbonate solution was added to the obtained residue, and the mixture was extracted with chloroform, and purified by silica gel column chromatography (chloroform:methanol=4:1+triethylamine 2%) to give 4-(1-methylpiperidin-4-yl)-2H-isoquinolin-1-one (88 mg) as white crystals.

Workup

  1. temperaturecooling
  2. additionwas added to the reaction mixture
  3. temperatureThe mixture was once heated
  4. temperatureunder reflux
  5. customthe solvent was evaporated
  6. additionAqueous potassium carbonate solution was added to the obtained residue
  7. extractionthe mixture was extracted with chloroform
  8. custompurified by silica gel column chromatography (chloroform:methanol=4:1+triethylamine 2%)

Sources & evidence

ORD record
ord-0e741d8f6fb54038b7f7b283502e6682
Source dataset
uspto-grants-2009_03
Patent number
US07501412B2

Reaction notes

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