1-Piperonylpiperazine → HCID 68522097, compound

HRID 884132Notes

Reaction equation

HRID 884132 reaction equation
[CH3:1][N:2]([CH2:20][C:21]([OH:23])=O)[C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][N:11]=2)=[C:5]([CH3:19])[CH:4]=1.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.[CH2:47]([N:57]1[CH2:62][CH2:61][NH:60][CH2:59][CH2:58]1)[C:48]1[CH:56]=[CH:55][C:54]2[O:53][CH2:52][O:51][C:50]=2[CH:49]=1>CN(C=O)C.O>[CH2:47]([N:57]1[CH2:62][CH2:61][N:60]([C:21](=[O:23])[CH2:20][N:2]([CH3:1])[C:3]2[CH:8]=[CH:7][C:6]([O:9][C:10]3[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][N:11]=3)=[C:5]([CH3:19])[CH:4]=2)[CH2:59][CH2:58]1)[C:48]1[CH:56]=[CH:55][C:54]2[O:53][CH2:52][O:51][C:50]=2[CH:49]=1

Participants

7

Reactant 4

HCID 944261-PiperonylpiperazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 68527414HCID 68527414, compound

Product 1

HCID 68522097HCID 68522097, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of {methyl[3-methyl-4-(5-nitropyridin-2-yloxy)phenyl]amino}acetic acid (0.93 g, 2.9 mmol) in DMF (40 mL) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.67 g, 3.5 mmol), 1-hydroxybenzotriazole monohydrate (0.54 g, 3.5 mmol), and 1-piperonylpiperazine (0.68 g, 3.08 mmol). The reaction mixture was stirred for 15 hours at room temperature under a nitrogen atmosphere. To the resulting solution was added water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1→dichloromethane methanol=100:1), to thereby yield 1.2 g of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1→dichloromethane methanol=100:1)

Sources & evidence

ORD record
ord-6e37ad66ca8a454f883c3c8ac8e3f515
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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