Hydrazine hydrate (1:1) → 3-Fluoro-4-(4-(4-methoxyphenyl)piperazin-1-yl)aniline

HRID 527197Notes

Reaction equation

HRID 527197 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[CH2:13][CH2:12]1.O.NN>[Pd].C(O)C>[F:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)[NH2:8]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 712952521-(2-Fluoro-4-nitrophenyl)-4-(4-methoxyphenyl)piperazine

Product 1

HCID 176097133-Fluoro-4-(4-(4-methoxyphenyl)piperazin-1-yl)anilineYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred suspension of compound 3 (0.2 g, 0.6 mmol) and palladium catalyst (10% Pd on carbon 0.04 g) in ethanol (6 mL), hydrazine monohydrate (0.29 mL, 5.7 mmol) was added slowly and the reaction mixture was heated to reflux for 4 h. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated to obtain amine 4 (0.17 g, 93%).

Workup

  1. additionwas added slowly
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux for 4 h
  4. filtrationthe reaction mixture was filtered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-995a58d3c8ae4d119d30a5e4da794ab4
Source dataset
uspto-grants-2016_05
Patent number
US09346791B2

Reaction notes

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