1-Methylpiperazine → 1-Methyl-4-[[3-(1-methylethoxy)-4-nitrophenyl]methyl]piperazine

HRID 518848Notes

Reaction equation

HRID 518848 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH:8]([O:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[N+:20]([O-:22])=[O:21])[CH:15]=O)([CH3:10])[CH3:9].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.C(O)(=O)C.CO>[CH:8]([O:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[N+:20]([O-:22])=[O:21])[CH2:15][N:5]1[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1)([CH3:10])[CH3:9]

Participants

8

Reactant 4

HCID 531671-MethylpiperazineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 62116082HCID 62116082, compound

Product 1

HCID 866980041-Methyl-4-[[3-(1-methylethoxy)-4-nitrophenyl]methyl]piperazine

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 1140TolueneSolvent2×

Procedure

3.25 ml of 1-methylpiperazine are added to a solution of 3.06 g of 3-isopropoxy-4-nitrobenzaldehyde in 15 ml of toluene and 0.34 ml of acetic acid in a three-necked round-bottomed flask under argon. The reaction mixture is stirred at ambient temperature for 1.5 h and then 5 ml of toluene are added, followed by 4.9 g of sodium triacetoxyborohydride by spatula. The reaction mixture is stirred at ambient temperature for 16 h, and then treated with 4.5 ml of methanol and 75 ml of a saturated sodium hydrogen carbonate solution. After stirring at ambient temperature for 30 min, the mixture is extracted with 30 ml and then 2×50 ml of ethyl acetate. The organic extracts are combined, washed with water, dried over magnesium sulfate, and then concentrated to dryness under reduced pressure, so as to give 4.24 g of 1-(3-isopropoxy-4-nitrobenzyl)-4-methylpiperazine in the form of a beige solid.

Workup

  1. stirringThe reaction mixture is stirred at ambient temperature for 16 h
  2. stirringAfter stirring at ambient temperature for 30 min
  3. extractionthe mixture is extracted with 30 ml
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-48189a867d1b4fd58540e06aecbe460a
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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