Ammonium formate → 2-Methyl-3-(piperazin-1-yl)quinoxaline

HRID 1727181Notes

Reaction equation

HRID 1727181 reaction equation
[CH3:1][C:2]1[C:11]([N:12]2[CH2:17][CH2:16][N:15](CC3C=CC=CC=3)[CH2:14][CH2:13]2)=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C([O-])=O.[NH4+]>CO.[Pd]>[CH3:1][C:2]1[C:11]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formate2×HCID 365893512-Methyl-3-[4-(phenylmethyl)piperazin-1-yl]quinoxaline

Product 1

HCID 28666102-Methyl-3-(piperazin-1-yl)quinoxaline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

To a solution of 2-methyl-3-[4-(phenylmethyl)piperazin-1-yl]quinoxaline (Preparation 19, 1.68 g, 5.28 mmol) in methanol (106 ml) was added ammonium formate (1.66 g, 26.4 mmol) followed by palladium (10% w/w on carbon, 0.25 g) under a nitrogen atmosphere. After 12.5 h, more ammonium formate (0.83 g, 13.2 mmol) and palladium (0.12 g) were added. The reaction mixture was filtered through Celite® and evaporated to a yellow oil. The crude product was purified by flash chromatography using silica gel eluting with methanol:dichloromethane (5:95 and then 10:90). The title compound was obtained as a pale yellow oil which crystallised upon standing (0.46 g, 38%).

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. customevaporated to a yellow oil
  3. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-80fb3be7923d49feb43e50bf4c1f15b1
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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