Hydrazine hydrate (1:1) → 4-[4-[4-(MethoxyMethoxy)phenyl]-1-piperazinyl]benzenaMine

HRID 527175Notes

Reaction equation

HRID 527175 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1.O.NN>CCO.[Pd]>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:12][CH2:13][N:14]([C:17]3[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=3)[CH2:15][CH2:16]2)=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 565937061-[4-(Methoxymethoxy)phenyl]-4-(4-nitrophenyl)piperazine

Product 1

HCID 565937074-[4-[4-(MethoxyMethoxy)phenyl]-1-piperazinyl]benzenaMineYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The nitro group in 11 (250.8 mg, 0.73 mmol) was reduced in the presence of 10% Pd/C (46.8 mg, 5% mole ratio) and hydrazine monohydrate (365.4 mg, 7.3 mmol) in EtOH (10 mL) at reflux. Once the starting material was fully consumed (about 3.5 h), the reaction mixture was filtered through a Celite pad and concentrated to afford 12 as white amorphous solid (226.5 mg, 99%), which was used directly for the next step without any purification: 1H NMR (400 MHz, CDCl3, δH) 7.07-6.81 (m, 6H), 6.72-6.63 (m, 2H), 5.13 (s, 2H), 3.49 (d, J=1.3 Hz, 3H), 3.46-3.34 (m, 2H), 3.22 (qd, J=7.1, 3.1 Hz, 8H); 13C NMR (100 MHz, CDCl3, δC) 151.53, 146.97, 144.63, 140.64, 119.05, 118.30, 117.51, 116.43, 95.36, 56.10, 51.45, 50.93. MALDI-MS: 314.2 (M+H+), 336.2 (M+Na+).

Workup

  1. temperatureat reflux
  2. customOnce the starting material was fully consumed (about 3.5 h)
  3. filtrationthe reaction mixture was filtered through a Celite pad
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b048cf3c399a4e46bb4401bae2e94a4a
Source dataset
uspto-grants-2016_05
Patent number
US09346791B2

Reaction notes

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