Formaldehyde → HCID 10445942, compound

HRID 1159520Notes

Reaction equation

HRID 1159520 reaction equation
Cl.[OH:2][CH2:3][CH:4]1[CH2:9][CH:8]([C:10]2[NH:11][C:12](=[O:20])[C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:7][CH2:6][NH:5]1.C=O.[C:23](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[CH3:23][N:5]1[CH2:6][CH2:7][CH:8]([C:10]2[NH:11][C:12](=[O:20])[C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:9][CH:4]1[CH2:3][OH:2]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 23082084HCID 23082084, compound

Product 1

HCID 10445942HCID 10445942, compoundYield 36.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

The obtained 3-(2-hydroxymethylpiperidin-4-yl)-2H-isoquinolin-1-one hydrochloride (433 mg) was dissolved in acetonitrile and water. 35% Formalin (340 μl) and sodium triacetoxy borohydride (697 mg) were added to the solution, and the mixture was stirred at room temperature for 20 min. The reaction mixture was alkalified with 20% aqueous potassium carbonate solution and extracted with chloroform. The chloroform layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine and dried over anhydrous magnesium sulfate. The drying agent was filtered off, and the solvent was concentrated. The precipitated crystals were washed with diethyl ether and dried under reduced pressure to give 3-(1-methyl-2-hydroxymethylpiperidin-4-yl)-2H-isoquinolin-1-one (146 mg).

Workup

  1. extractionextracted with chloroform
  2. washThe chloroform layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe drying agent was filtered off
  5. concentrationthe solvent was concentrated
  6. washThe precipitated crystals were washed with diethyl ether
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-6880a8afeb48461ba4de7d9371f37544
Source dataset
uspto-grants-2010_10
Patent number
US07812178B2

Reaction notes

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