Acetic Acid → 1-Methyl-4-(1-(4-nitrophenyl)piperidin-4-yl)piperazine

HRID 2189266Notes

Reaction equation

HRID 2189266 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][C:13](=O)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:17][N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.CC(O)=O.[BH3-]C#N.[Na+]>CO>[CH3:17][N:18]1[CH2:23][CH2:22][N:21]([CH:13]2[CH2:14][CH2:15][N:10]([C:7]3[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)[CH2:11][CH2:12]2)[CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 531671-MethylpiperazineHCID 38425621-(4-Nitrophenyl)piperidin-4-oneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 580159221-Methyl-4-(1-(4-nitrophenyl)piperidin-4-yl)piperazineYield 39.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-(4-Nitro-phenyl)-piperidin-4-one (84 mg, 0.38 mmol) and 1-methylpiperazine (0.085 mL, 0.76 mmol) in MeOH (2 mL) is stirred at room temperature for 5 hours. Then to the reaction mixture is added 0.2 mL of HOAc, followed by NaCNBH3 (72 mg, 1.14 mmol). The mixture is stirred at room temperature for 0.5 hour, then concentrated. The residue is taken up in EtOAc, washed with saturated NaHCO3 aqueous solution and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product is purified by column chromatography (SiO2, 2N NH3 in MeOH:CH2Cl2=1:99 to 10:90) to give 46 mg of the title compound as a yellow solid.

Workup

  1. stirringThe mixture is stirred at room temperature for 0.5 hour
  2. concentrationconcentrated
  3. washwashed with saturated NaHCO3 aqueous solution and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product is purified by column chromatography (SiO2, 2N NH3 in MeOH:CH2Cl2=1:99 to 10:90)

Sources & evidence

ORD record
ord-d66d5ef12b8740ffabd8995f1de8272c
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

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