Hydrazine hydrate (1:1) → 4-[4-(1-Methylethyl)-1-piperazinyl]-2,5-bis(methyloxy)aniline

HRID 1014213Notes

Reaction equation

HRID 1014213 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[C:6]([O:12][CH3:13])=[CH:5][C:4]=1[N:14]1[CH2:19][CH2:18][N:17]([CH:20]([CH3:22])[CH3:21])[CH2:16][CH2:15]1.O.NN>CO>[CH3:22][CH:20]([N:17]1[CH2:18][CH2:19][N:14]([C:4]2[C:3]([O:2][CH3:1])=[CH:8][C:7]([NH2:9])=[C:6]([O:12][CH3:13])[CH:5]=2)[CH2:15][CH2:16]1)[CH3:21]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 594421271-[2,5-Bis(methyloxy)-4-nitrophenyl]-4-(1-methylethyl)piperazine

Product 1

HCID 594417344-[4-(1-Methylethyl)-1-piperazinyl]-2,5-bis(methyloxy)anilineYield 63.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-[2,5-bis(methyloxy)-4-nitrophenyl]-4-(1-methylethyl)piperazine (3.50 g, 11.3 mmol), FeCl3 (0.550 g, 3.4 mmol), activated carbon (4.0 g), and hydrazine hydrate (3.6 mL, 113 mmol) was heated in methanol (50 mL) for 3 hours. The mixture was filtered over celite and concentrated to give 4-[4-(1-methylethyl)-1-piperazinyl]-2,5-bis(methyloxy)aniline as a grey solid (2.00 g, 7.17 mmol, 63% yield). 1H NMR (400 MHz, CDCl3) δ ppm 1.10 (d, J=6.60 Hz, 6 H), 2.72 (s, 5 H), 3.03 (s, 4H), 3.59 (s, 2 H), 3.78 (s, 3 H), 3.79 (s, 3 H), 6.34 (s, 1 H), 6.57 (s, 1 H).

Workup

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

Sources & evidence

ORD record
ord-0f9dfbb0a577479ca0028c200721b233
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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