Formaldehyde → HCID 135453965, compound

HRID 1783314Notes

Reaction equation

HRID 1783314 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([C:8]2[C:20]3[C:19]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[C:13](=[O:21])[NH:12][C:11]=3[N:10]([CH3:22])[N:9]=2)[CH2:4][CH2:3]1.C=O.[C:25](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O>[CH3:25][N:2]1[CH2:3][CH2:4][CH:5]([C:8]2[C:20]3[C:19]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[C:13](=[O:21])[NH:12][C:11]=3[N:10]([CH3:22])[N:9]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 135621716HCID 135621716, compound

Product 1

HCID 135453965HCID 135453965, compoundYield 54.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-(Piperidin-4-yl)-3-methyl-pyrazolo[3,4-c]isoquinolin-5(4H)-one hydrochloride (1.0 g) obtained in Example 227 and 35% aqueous formalin solution (0.53 g) were suspended in water (20 mL), and sodium triacetoxyborohydride (1.3 g) was added at room temperature, and the mixture was stirred for 1 hr. After the completion of the reaction, the solvent was evaporated, and aqueous potassium carbonate solution was added to the obtained residue. The mixture was extracted with a mixed solvent (chloroform:methanol=10:1), and the organic layer was dried over magnesium sulfate. The solvent was evaporated, and ethanol was added to the precipitated crystals. The precipitated crystals was collected by filtration and washed with ethyl acetate to give 1-(1-methylpiperidin-4-yl)-3-methyl-pyrazolo[3,4-c]isoquinolin-5(4H)-one (0.51 g) as pale-brown crystals.

Workup

  1. customAfter the completion of the reaction
  2. customthe solvent was evaporated
  3. additionaqueous potassium carbonate solution was added to the obtained residue
  4. extractionThe mixture was extracted with a mixed solvent (chloroform:methanol=10:1)
  5. dry with materialthe organic layer was dried over magnesium sulfate
  6. customThe solvent was evaporated
  7. additionethanol was added to the precipitated crystals
  8. filtrationThe precipitated crystals was collected by filtration
  9. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-b1b8d7b8362444ac879111cc04c7b82c
Source dataset
uspto-grants-2009_03
Patent number
US07501412B2

Reaction notes

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