Piperazine → (4-Methylpiperazin-1-yl)(4-nitrophenyl)methanone
Reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=1)([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:8]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)=[O:10])[CH2:15][CH2:14]1Participants
Procedure
4-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 (4-Methyl-piperazin-1-yl)-(4-nitro-phenyl)-methanone. (M+H)=250.6. 1H NMR (400 MHz, DMSO, d6) δ 8.28 (d, 2H, J=8.40 Hz), 7.67 (d, 2H, J=8.42 Hz), 3.64 (m, 2H), 3.25 (m, 2H), 2.38 (m, 2H), 2.26 (m, 2H), 2.20 (s, 3H).
Workup
- extractionorganics were extracted with ethyl acetate/dichloromethane
- dry with materialCombined organics were dried over sodium sulfate
- filtrationfiltered
- customThe crude mixture was purified by Isco flash column chromatography (Hexane/Ethyl Acetate)
Sources & evidence
- ORD record
- ord-58ef333582e8405f8b38636d2c21f427
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08471005B2
Reaction notes
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