Formaldehyde → 1-Hydroxymethyl-3-(1-methyl-4-piperidinyl)-1H-indazole

HRID 867676Notes

Reaction equation

HRID 867676 reaction equation
[CH2:1]=[O:2].[CH3:3][N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][N:11]=2)[CH2:6][CH2:5]1.[OH-].[Na+]>C(O)C>[OH:2][CH2:1][N:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]([CH:7]2[CH2:6][CH2:5][N:4]([CH3:3])[CH2:9][CH2:8]2)=[N:11]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 178480237HCID 178480237, compound

Product 1

HCID 140325041-Hydroxymethyl-3-(1-methyl-4-piperidinyl)-1H-indazoleYield 57.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 0.52 g of paraformaldehyde, 3.0 g of 3-(1-methyl-4-piperidinyl)-1H-indazole, 15 ml of ethanol and 0.34 ml of 5% aqueous sodium hydroxide was refluxed for 3 hrs. The ethanol was removed in vacuo and the residue diluted with water. The aqueous suspension was extracted with dichloromethane (2x, 50 ml) and the combined extracts were washed with water and dried over anhydrous magnesium sulfate. The dichloromethane was evaporated in vacuo to yield an oil, which crystallized upon standing. The solid was recrystallized twice from ethyl acetate to yield 1.3 g (57.8%) of product, mp 128°-130° C.

Workup

  1. customThe ethanol was removed in vacuo
  2. additionthe residue diluted with water
  3. extractionThe aqueous suspension was extracted with dichloromethane (2x, 50 ml)
  4. washthe combined extracts were washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe dichloromethane was evaporated in vacuo
  7. customto yield an oil, which
  8. customcrystallized
  9. customThe solid was recrystallized twice from ethyl acetate

Sources & evidence

ORD record
ord-b1cd6f65f9114292a63255529ebe0fe6
Source dataset
uspto-grants-1988_10
Patent number
US04775761

Reaction notes

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