Water → HCID 67238980, compound

HRID 880486Notes

Reaction equation

HRID 880486 reaction equation
[CH3:1][CH:2]([CH3:6])[C:3](=O)[CH3:4].[N+:7]([C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[CH:12][CH:11]=1)([O-:9])=[O:8].C([BH3-])#N.[Na+].O>CO.C(O)(=O)C>[CH3:4][CH:3]([N:19]1[CH2:20][CH2:21][N:16]([C:13]2[CH:12]=[CH:11][C:10]([N+:7]([O-:9])=[O:8])=[CH:15][CH:14]=2)[CH2:17][CH2:18]1)[CH:2]([CH3:6])[CH3:1]

Participants

7

Reactant 4

HCID 962WaterHCID 112513-Methyl-2-butanoneHCID 804471-(4-Nitrophenyl)piperazineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 67238980HCID 67238980, compoundYield 34.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

3-Methyl-2-butanone (0.76 mL, 7.24 mmol) was added to a solution of 1-(4-nitrophenyl)piperazine (1.0 g, 4.83 mmol) in methanol (10 mL) and acetic acid (1 mL) and stirred for 30 min at ambient temperature. Sodium cyanoborohydride (1.81 g, 28.98 mmol) was added and the mixture refluxed for 12 h, cooled and then poured into water and extracted with ethyl acetate. The combined organic layers were washed with water, brine, dried over anhydrous sodium sulfate and concentrated in vacuo to afford the crude product. Purification by column chromatography over silica gel (100-200 mesh) using 5-10% ethyl acetate/petroleum ether as eluent afforded 1-(1,2-Dimethylpropyl)-4-(4-nitrophenyl)piperazine (0.46 g, 34%).

Workup

  1. temperaturethe mixture refluxed for 12 h
  2. temperaturecooled
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with water, brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto afford the crude product
  8. customPurification by column chromatography over silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-d8a4f204ab174dbc8035c0a19d9cc344
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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