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

HRID 1064077Notes

Reaction equation

HRID 1064077 reaction equation
[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

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 4311764Sodium borohydrideHCID 9928554HCID 9928554, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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)−.

Workup

  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

Sources & evidence

ORD record
ord-56a9d3d970bd49648c2fa4c015eb334c
Source dataset
uspto-grants-2005_11
Patent number
US06967254B2

Reaction notes

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