1-[3-(2-Methoxy-5-nitrophenoxy)propyl]-4-methylpiperazine → 4-Methoxy-3-[3-(4-methylpiperazin-1-yl)propoxy]aniline

HRID 1593786Notes

Reaction equation

HRID 1593786 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]1.[H][H]>C(O)(C)C.[Pd]>[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]1

Participants

5

Reactant 2

HCID 468640581-[3-(2-Methoxy-5-nitrophenoxy)propyl]-4-methylpiperazineHCID 178418361HCID 178418361, compound2×

Product 1

HCID 589997944-Methoxy-3-[3-(4-methylpiperazin-1-yl)propoxy]aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

To a solution of 1-[3-(2-methoxy-5-nitro-phenoxy)-propyl]-4-methyl-piperazine (2.5 g, 8.1 mmol) in 25 mL of iso-propanol was added 10% Pd-C (0.25 g, 10 wt. %). This mixture was shaken under 35-40 psi of hydrogen in a Parr shaker until hydrogen uptake ceased. The reaction mixture was purged with nitrogen and filtered through celite. The resulting solution was concentrated in vacuo to give the crude 4-methoxy-3-[3-(4-methyl-piperazin-1-yl)-propoxy]-phenylamine as a yellow oil which was used directly in the coupling step described below. 1H NMR (300 MHz, CDCl3) δ 6.71 (d, J=8 Hz, 1H), 6.33 (d, J=2.4 Hz, 1H), 6.23 (dd, J=2.4, 8 Hz, 1H), 4.05 (t, J=8 Hz, 2H), 3.80 (s, 3H), 2.53 (m,10H), 2.30 (s, 3H), 2.02 (m, 2H).

Workup

  1. customThe reaction mixture was purged with nitrogen
  2. filtrationfiltered through celite
  3. concentrationThe resulting solution was concentrated in vacuo

Sources & evidence

ORD record
ord-4cfc8596a935428294a254dcdbf27425
Source dataset
uspto-grants-2007_11
Patent number
US07297795B2

Reaction notes

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