Water → Methyl 3-[4-(4-nitrophenyl)piperazinyl]propanoate

HRID 2353224Notes

Reaction equation

HRID 2353224 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:16][O:17][C:18](=[O:22])[CH2:19][CH2:20]Br.O.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH3:16][O:17][C:18](=[O:22])[CH2:19][CH2:20][N:13]1[CH2:14][CH2:15][N:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 962WaterHCID 76934Methyl 3-bromopropanoateHCID 804471-(4-Nitrophenyl)piperazineHCID 516892Sodium Bicarbonate

Product 1

HCID 16450139Methyl 3-[4-(4-nitrophenyl)piperazinyl]propanoateYield 63.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(4-nitro-phenyl)-piperazine (2 g, 9.66 mmol) in DMF (10 mL) was added 3-bromopropionic acid methyl ester (1.6 g, 9.66 mmol) and the mixture was stirred at ambient temperature for 16 h. Water was added to the reaction, followed by adjusting pH to 7 with sat. aqueous NaHCO3. The resulting precipitate was collected by filtration and washed with water to furnish the title compound as a yellow solid (1.8 g, 63.6%): MS (ESI) m/z 294 (M+H); 1H NMR (400 MHz, CDCl3) δ 2.55 (t, J=7.2 Hz, 2H), 2.62 (t, J=4.8 Hz, 4H), 2.77 (t, J=6.8 Hz, 2H), 3.42 (t, J=5.2 Hz, 4H), 3.71 (s, 3H), 6.81-6.83 (m, 2H), 8.11-8.14 (m, 2H).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-8ba31f627f8e48af9fb8293e3816a0c8
Source dataset
uspto-grants-2010_07
Patent number
US07750012B2

Reaction notes

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