1-Benzylpiperazine → 2-Methyl-3-[4-(phenylmethyl)piperazin-1-yl]quinoxaline

HRID 1727182Notes

Reaction equation

HRID 1727182 reaction equation
Cl[C:2]1[C:11]([CH3:12])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH2:13]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])O.[Na+]>>[CH3:12][C:11]1[C:2]([N:23]2[CH2:24][CH2:25][N:20]([CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:21][CH2:22]2)=[N:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[N:10]=1

Participants

4

Reactant 3

HCID 759941-BenzylpiperazineHCID 2362762-Chloro-3-methylquinoxalineHCID 516892Sodium Bicarbonate

Product 1

HCID 365893512-Methyl-3-[4-(phenylmethyl)piperazin-1-yl]quinoxaline

Conditions

Temperature
125 °C

Procedure

2-Chloro-3-methylquinoxaline (1.0 g, 5.6 mmol) and N-benzylpiperazine (2.9 ml, 16.8 mmol) were mixed and heated to 125° C. for 18 h. Saturated aqueous sodium hydrogen carbonate was added and the product was extracted with chloroform. The combined organic extracts were dried (Na2SO4) and concentrated in vacuo to give a dark red oil. The crude product was purified by flash chromatography using silica gel eluting with methanol:dichloromethane (15:85) to give the pure product as a red oil which solidified upon standing (1.63 g, 94%).

Workup

  1. extractionthe product was extracted with chloroform
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customto give a dark red oil
  5. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-820d603c06c347b0b94ae6b9ced3d67e
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

Loading…