Acetic Acid → 1-Methyl-4-[(2-methyl-3-nitrophenyl)methyl]piperazine

HRID 419332Notes

Reaction equation

HRID 419332 reaction equation
[CH3:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.CC(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:13][N:14]1[CH2:19][CH2:18][N:17]([CH2:4][C:3]2[CH:6]=[CH:7][CH:8]=[C:9]([N+:10]([O-:12])=[O:11])[C:2]=2[CH3:1])[CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 531671-MethylpiperazineHCID 2622412-Methyl-3-nitrobenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 594279041-Methyl-4-[(2-methyl-3-nitrophenyl)methyl]piperazineYield 100%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

2-Methyl-3-nitrobenzaldehyde (J. Org. Chem. 1981, 46, 1752-1755) (1.0 g, 6.1 mmol) was dissolved in DCE and N-methylpiperazine and HOAc were added followed by sodium triacetoxyborohydride. The reaction was stirred at rt for 1 h and was then quenched with 5% K2CO3 solution. The reaction mixture was extracted (3×) with ethyl acetate, dried over magnesium sulfate, filtered, concentrated onto silica gel and flash chromatographed to give the title compound (1.6 g, 100%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.69 (d, J=7.7 Hz, 1H), 7.52 (d, J=7.5 Hz, 1H), 7.34 (t, J=7.9 Hz, 1H), 3.48 (s, 2H), 2.16-2.42 (m, 1H), 2.10 (s, 3H).

Workup

  1. customwas then quenched with 5% K2CO3 solution
  2. extractionThe reaction mixture was extracted (3×) with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated onto silica gel and flash
  6. customchromatographed

Sources & evidence

ORD record
ord-ccb088199dd14999be603dc914b0597b
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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