Hydrazine hydrate (1:1) → HCID 55234557, compound

HRID 1014209Notes

Reaction equation

HRID 1014209 reaction equation
[CH:1]1([CH2:4][N:5]2[CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[C:13]([O:20][CH3:21])[CH:12]=3)[CH2:7][CH2:6]2)[CH2:3][CH2:2]1.O.NN>CO>[CH:1]1([CH2:4][N:5]2[CH2:6][CH2:7][N:8]([C:11]3[CH:16]=[CH:15][C:14]([NH2:17])=[C:13]([O:20][CH3:21])[CH:12]=3)[CH2:9][CH2:10]2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59442123HCID 59442123, compound

Product 1

HCID 55234557HCID 55234557, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-(cyclopropylmethyl)-4-[3-(methyloxy)-4-nitrophenyl]piperazine (1.05 g, 3.41 mmol), FeCl3 (0.165 g, 1.02 mmol), activated carbon (1.0 g), and hydrazine hydrate (1.3 mL, 41 mmol) was heated in methanol (50 mL) for 3 hours. Once the starting material was judged consumed by thin layer chromatography (10% MeOH/CH2CL2) the mixture was filtered over celite and concentrated to give 4-[4-(cyclopropylmethyl)-1-piperazinyl]-2-(methyloxy)aniline as a yellow solid (0.800 g, 3.07 mmol, 90% yield). 1H NMR (400 MHz, CDCl3) δ ppm 0.15 (q, J=4.89 Hz, 2 H), 0.52-0.60 (m, 2 H), 0.94 (d, J=6.23 Hz, 1 H), 2.35 (d, J=6.59 Hz, 2 H), 2.74 (s, 4 H), 3.07-3.15 (m, 4 H), 3.53 (s, 2 H), 3.83 (s, 3 H), 6.43 (dd, J=8.43, 2.20 Hz, 1 H), 6.53 (d, J=2.20 Hz, 1 H), 6.65 (d, J=8.06 Hz, 1 H).

Workup

  1. customOnce the starting material was judged consumed by thin layer chromatography (10% MeOH/CH2CL2) the mixture
  2. filtrationwas filtered over celite and
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d815430a239440348e9da990b7671c3f
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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