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

HRID 986113

Reaktionsgleichung

Reaktionsgleichung von HRID 986113
[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

Komponenten

5

Edukt 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 178480237HCID 178480237, Verbindung

Produkt 1

HCID 140325041-Hydroxymethyl-3-(1-methyl-4-piperidinyl)-1H-indazoleAusbeute 57,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-2cbc01f5374b4d74bd0aee0b14a5c6c3
Quelldatensatz
uspto-grants-1987_12
Patentnummer
US04710573

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