1-Methyl-4-{2-[3-(ethyloxy)-4-nitrophenyl]ethyl}piperazine → 2-(Ethyloxy)-4-[2-(4-methyl-1-piperazinyl)ethyl]aniline

HRID 419497Notes

Reaction equation

HRID 419497 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[C:12]([O:19][CH2:20][CH3:21])[CH:11]=2)[CH2:4][CH2:3]1>CCOC(C)=O.CO>[CH2:20]([O:19][C:12]1[CH:11]=[C:10]([CH2:9][CH2:8][N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)[CH:15]=[CH:14][C:13]=1[NH2:16])[CH3:21]

Participants

3

Reactant 1

HCID 594527831-Methyl-4-{2-[3-(ethyloxy)-4-nitrophenyl]ethyl}piperazine

Product 1

HCID 594528212-(Ethyloxy)-4-[2-(4-methyl-1-piperazinyl)ethyl]anilineYield 101.8%

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

1-methyl-4-{2-[3-(ethyloxy)-4-nitrophenyl]ethyl}piperazine (0.373 g, 1.14 mmol) was placed in a 100 mL high pressure vessel and dissolved in 30 mL of 1 to 1 EtOAc/MeOH. 5 wt % Platinum(sulfided)/carbon (0.223 g, 0.057 mmol) was added followed quickly by a screw cap septum. The flask was evacuated and filled with N2 six times to remove any oxygen. The vessel was then pressurized with H2 (balloon). The solution stirred overnight. The next morning the vessel was evacuated and filled with N2 six times to remove any H2. The solution was filtered through celite and evaporated to afford the title compound of step D (0.308 g, 1.16 mmol, 100%). 1H NMR (400 MHz, CDCl3) δ ppm 6.57-6.65 (m, 3H), 3.99-4.08 (m, 2H), 3.62-3.74 (m, 2H), 2.65-2.75 (m, 2H), 2.47-2.59 (m, 8H), 2.31 (s, 3H), 1.36-1.45 (m, 3H).

Workup

  1. customcap septum
  2. customThe flask was evacuated
  3. additionfilled with N2 six times
  4. customto remove any oxygen
  5. customThe next morning the vessel was evacuated
  6. additionfilled with N2 six times
  7. customto remove any H2
  8. filtrationThe solution was filtered through celite
  9. customevaporated

Sources & evidence

ORD record
ord-fc06f982371b47c6beeadb9e05dc61bf
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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