Piperazine → (4-Methylpiperazin-1-yl)(3-nitrophenyl)methanone

HRID 1261994Notes

Reaction equation

HRID 1261994 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=O)([O-:3])=[O:2].[NH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.Cl.[CH3:20]N(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.O1CCCC1.C(=O)(O)[O-].[Na+]>>[CH3:20][N:13]1[CH2:18][CH2:17][N:16]([C:7]([C:6]2[CH:10]=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)=[O:9])[CH2:15][CH2:14]1

Participants

7

Reactant 6

HCID 4837PiperazineHCID 8028TetrahydrofuranHCID 84973-Nitrobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 763411(4-Methylpiperazin-1-yl)(3-nitrophenyl)methanone

Procedure

m-Nitrobenzoic acid (2.00 g, 0.0120 mol), piperazine, 1-methyl- (1.44 g, 0.0144 mol), N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (2.29 g, 0.0120 mol) and 1-Hydroxybenzotriazole (0.40 g, 0.0030 mol) were dissolved in Tetrahydrofuran (35 mL, 0.43 mol) and the reaction was allowed to stir overnight at room temperature. The reaction mixture was poured over saturated sodium bicarbonate, and organics were extracted with ethyl acetate/dichloromethane. Combined organics were dried over sodium sulfate, filtered and reduced en vacuo. The crude mixture was purified by Isco flash column chromatography (Hexane/Ethyl Acetate). Combined fractions were reduced en vacuo to afford 2.46 g of (4-Methyl-piperazin-1-yl)-(3-nitro-phenyl)-methanone. (M+H)=250.6.

Workup

  1. extractionorganics were extracted with ethyl acetate/dichloromethane
  2. dry with materialCombined organics were dried over sodium sulfate
  3. filtrationfiltered
  4. customThe crude mixture was purified by Isco flash column chromatography (Hexane/Ethyl Acetate)

Sources & evidence

ORD record
ord-25f2fe0ef96e4d6e8018e4e12bd3ea78
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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