Hydrazine hydrate (1:1) → 2-(Methyloxy)-4-(4-propyl-1-piperazinyl)aniline

HRID 1014206Notes

Reaction equation

HRID 1014206 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH3:20])[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O.O.NN>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:13][CH2:14][N:15]([CH2:18][CH2:19][CH3:20])[CH2:16][CH2:17]2)[CH:6]=[CH:7][C:8]=1[NH2:9]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 598602661-[3-(Methyloxy)-4-nitrophenyl]-4-propylpiperazine

Product 1

HCID 598602822-(Methyloxy)-4-(4-propyl-1-piperazinyl)anilineYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-[3-(methyloxy)-4-nitrophenyl]-4-propylpiperazine (Intermediate B50, 1.5 g, 5.4 mmol), FeCl3 (0.300 g, 1.85 mmol), activated carbon (2.0 g), and hydrazine hydrate (2.1 mL, 65 mmol) was heated in methanol (50 mL) for 3 hours. The mixture was filtered over celite and concentrated to give 2-(methyloxy)-4-(4-propyl-1-piperazinyl)aniline as a white solid (1.03 g, 4.2 mmol, 78% yield). 1H NMR (400 MHz, CDCl3) δ ppm 0.93 (t, J=7.51 Hz, 3 H), 1.51-1.61 (m, 2 H), 2.37 (d, J=8.06 Hz, 2 H), 2.57-2.66 (m, 4 H), 3.09-3.10 (m, 4 H), 3.53 (s, 2 H), 3.83 (s, 3 H), 6.42 (dd, J=8.24, 2.38 Hz, 1H), 6.52 (d, J=2.20 Hz, 1 H), 6.64 (d, J=8.42 Hz, 1 H).

Workup

  1. filtrationThe mixture was filtered over celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-e80c805e0ae34202b6c6d5979a8b8a0d
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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