Potassium Carbonate → 2-[N-[3-(4-Nitrophenoxy)propyl]methylamino methyl]quinoxaline

HRID 1091085Notes

Reaction equation

HRID 1091085 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:13]=[N:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.C(=O)([O-])[O-].[K+].[K+].[N+:20]([C:23]1[CH:33]=[CH:32][C:26]([O:27][CH2:28][CH2:29][CH2:30]I)=[CH:25][CH:24]=1)([O-:22])=[O:21]>C(#N)C.C(O)C>[N+:20]([C:23]1[CH:33]=[CH:32][C:26]([O:27][CH2:28][CH2:29][CH2:30][N:2]([CH2:3][C:4]2[CH:13]=[N:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH3:1])=[CH:25][CH:24]=1)([O-:22])=[O:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15675889N-Methyl-1-(quinoxalin-2-yl)methanamineHCID 156758901-(4-Nitrophenoxy)-3-iodopropane

Product 1

HCID 156758912-[N-[3-(4-Nitrophenoxy)propyl]methylamino methyl]quinoxalineYield 83.1%

Reagents, catalysts & solvents 1

HCID 21984225Acetonitrile ethanolSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred suspension of 2-(methylaminomethyl)quinoxaline (1.10 g, 6.35 mmol) and potassium carbonate (0.88 g, 6.35 mmol) in 2:1 acetonitrile/ethanol (40 mL) was added 1-(4-nitrophenoxy)-3-iodopropane (1.95 g, 6.35 mmol). The resulting mixture was heated at 85° C. overnight, concentrated, and partitioned between ethyl acetate and 10% aqueous potassium carbonate. The organic phase was dried (MgSO4), decolorized (charcoal), and concentrated to afford 1.86 g (83%) of product as a yellow semi-solid which was of sufficient purity to use in the next step.

Workup

  1. concentrationconcentrated
  2. custompartitioned between ethyl acetate and 10% aqueous potassium carbonate
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ba95addf695e4dfb953cfc593aaa0804
Source dataset
uspto-grants-1992_01
Patent number
US05084463

Reaction notes

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