1-(4-Nitrophenyl)-4-(oxetan-3-yl)piperazine → 4-(4-(Oxetan-3-yl)piperazin-1-yl)aniline

HRID 1024077Notes

Reaction equation

HRID 1024077 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([CH:16]3[CH2:19][O:18][CH2:17]3)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O>[Pd].C(O)C>[O:18]1[CH2:19][CH:16]([N:13]2[CH2:12][CH2:11][N:10]([C:7]3[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=3)[CH2:15][CH2:14]2)[CH2:17]1

Participants

4

Reactant 1

HCID 866841521-(4-Nitrophenyl)-4-(oxetan-3-yl)piperazine

Product 1

HCID 681947994-(4-(Oxetan-3-yl)piperazin-1-yl)anilineYield 90.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A 250-mL round-bottomed flask was purged with nitrogen and charged with 117d (1.5 g, 5.7 mmol), 10% palladium on carbon (50% wet, 750 mg), and ethanol (60 mL). The flask was evacuated, charged with hydrogen gas, and stirred at room temperature for 15 h. The hydrogen was then evacuated and nitrogen charged into the flask. The catalyst was removed by filtration through a pad of Celite and the filtrate was concentrated under reduced pressure to afford 117e (1.2 g, 90%), which was used in the next step without further purification. MS: [M+H]+ 234

Workup

  1. customA 250-mL round-bottomed flask was purged with nitrogen
  2. customThe flask was evacuated
  3. additioncharged with hydrogen gas
  4. customThe hydrogen was then evacuated
  5. additionnitrogen charged into the flask
  6. customThe catalyst was removed by filtration through a pad of Celite
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0e9c5a999e9e4745bf362dcb337ee23f
Source dataset
uspto-grants-2014_05
Patent number
US08722676B2

Reaction notes

Loading…