Formaldehyde → 4-(4-Chlorophenyl)-1-(1-methyl-piperidin-4-yl)-5-pyridin-4-yl-1,2-dihydro-pyrazol-3-one

HRID 1064077Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1064077
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:25])[NH:10][N:11]([CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[CH2:26]=O.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:25])[NH:10][N:11]([CH:19]3[CH2:20][CH2:21][N:22]([CH3:26])[CH2:23][CH2:24]3)[C:12]=2[C:13]2[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 712FormaldehydeHCID 4311764Sodium borohydrideHCID 9928554HCID 9928554, Verbindung

Produkt 1

HCID 100904564-(4-Chlorophenyl)-1-(1-methyl-piperidin-4-yl)-5-pyridin-4-yl-1,2-dihydro-pyrazol-3-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 4-(4-chlorophenyl)-1-piperidin-4-yl-5-pyridin-4-yl-1,2-dihydro-pyrazol-3-one (0.12 g, 0.34 mmol) in anhydrous methanol (3 mL) was cooled to 0° C. in an ice-water bath and added formaldehyde (3 mL; 37 wt. % in water), followed by sodium borohydride (0.039 g, 1 mmol). After stirring for 1 hour, the reaction was quenched with water and diluted with methylene chloride. The organic layer was washed with brine, dried (Na2SO4), and concentrated in vacuo. The title compound was isolated as a yellow amorphous solid by preparative HPLC. MS (ES+): 369.2 (M+H)+; (ES−): 367.1 (M−H)−.

Aufarbeitung

  1. customthe reaction was quenched with water
  2. additiondiluted with methylene chloride
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-56a9d3d970bd49648c2fa4c015eb334c
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06967254B2

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