HCID 59452668, compound → 2-Methoxy-4-[2-(4-methylpiperazin-1-yl)ethyl]aniline

HRID 419462Notes

Reaction equation

HRID 419462 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][CH3:20])[CH:11]=2)[CH2:4][CH2:3]1>CCOC(C)=O.CO>[CH3:20][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]

Participants

3

Reactant 1

HCID 59452668HCID 59452668, compound

Product 1

HCID 574161632-Methoxy-4-[2-(4-methylpiperazin-1-yl)ethyl]anilineYield 86%

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

1-Methyl-4-{2-[3-(methyloxy)-4-nitrophenyl]ethyl}piperazine (0.6 g, 2.15 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 (0.42 g, 0.107 mmol) was added followed quickly by a rubber septum. The flask was evacuated and filled with N2 six times to remove any oxygen. The vessel was then pressurized with H2 (50 psi). 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 (0.460 g, 1.84 mmol, 86%). 1H NMR (400 MHz, CDCl3) δ ppm 6.60-6.64 (m, 3H), 3.82 (s, 3H), 3.64 (bs, 2H), 2.64-2.73 (m, 2H), 2.38-2.63 (m, 10H), 2.29 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-b5b519374f5245b2b8384b78c3629d47
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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