Hydrazine hydrate (1:1) → HCID 59441949, compound

HRID 1014208Notes

Reaction equation

HRID 1014208 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH:19]([CH3:21])[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][CH:19]([CH3:21])[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 59441661HCID 59441661, compound

Product 1

HCID 59441949HCID 59441949, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-[3-(methyloxy)-4-nitrophenyl]-4-(2-methylpropyl)piperazine (1.7 g, 5.82 mmol), FeCl3 (0.280 g, 1.75 mmol), activated carbon (2.0 g), and hydrazine hydrate (2.23 mL, 70 mmol) was heated in methanol (50 mL) for 3 hours. The mixture was filtered over celite and concentrated to give 2-(methyloxy)-4-[4-(2-methylpropyl)-1-piperazinyl]aniline as a white solid (1.24 g, 4.80 mmol, 83% yield). 1H NMR (400 MHz, CDCl3) δ ppm 0.94 (d, J=6.22 Hz, 6 H), 1.85 (s, 1 H), 2.20 (s, 2 H), 2.61 H), 3.10 (s, 4 H), 3.54 (s, 2 H), 3.83 (s, 3 H), 6.43 (m, 1 H), 6.52 (d, J=1.83 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-879a331363e146e29c6382894d7715ba
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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