Piperazine → HCID 10269950, compound

HRID 1282305Notes

Reaction equation

HRID 1282305 reaction equation
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[N:11][C:10]2[C:9]([C:15](Cl)=[O:16])=[C:8]([CH3:18])[C:7]([N+:19]([O-:21])=[O:20])=[CH:6][C:5]=2[N:4]=1.[NH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>>[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[N:11][C:10]2[C:5](=[CH:6][C:7]([N+:19]([O-:21])=[O:20])=[C:8]([CH3:18])[C:9]=2[C:15]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[O:16])[N:4]=1

Participants

3

Reactant 2

HCID 4837PiperazineHCID 10805016HCID 10805016, compound

Product 1

HCID 10269950HCID 10269950, compound

Procedure

Prepared from 2,3-dimethoxy-6-methyl-7-nitro-quinoxaline-5-carbonyl chloride (13) 250 mg (0.80 mmol) and piperazine 138 mg (1.60 mmol). Reaction was continued for 2 hours, and the crude product was eluted through a flash column (8% methanol in chloroform): 250 mg (86%), mp 150-152° C.; 1H NMR (CDCl3): δ 8.30 (s, 1H), 4.05 (s, 3H), 3.96 (s, 3H), 3.81 (t, 4H, J=4.9, 5.1 Hz), 2.96 (t, 4H, J=5.1, 4.9 Hz), 2.54 (s, 3H), 1.84 (br s, 1H); MS (APCI): m/z 362 (M+H). Anal. Calcd. for C16H19N5O5: C, 53.18; H, 5.30; N, 19.38. Found: C, 53.08; H, 5.22; N, 18.82.

Workup

  1. customReaction
  2. washthe crude product was eluted through a flash column (8% methanol in chloroform)

Sources & evidence

ORD record
ord-b6681055ee5a46cab07f37fdd6ca2800
Source dataset
uspto-grants-2002_09
Patent number
US06455698B1

Reaction notes

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