5-Nitro-2-(4-(oxetan-3-yl)piperazin-1-yl)benzonitrile → HCID 86704502, compound

HRID 633405Notes

Reaction equation

HRID 633405 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:12]2[CH2:17][CH2:16][N:15]([CH:18]3[CH2:21][O:20][CH2:19]3)[CH2:14][CH2:13]2)=[C:8]([CH:11]=1)[C:9]#[N:10])([O-])=O>CCO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([N:12]2[CH2:17][CH2:16][N:15]([CH:18]3[CH2:19][O:20][CH2:21]3)[CH2:14][CH2:13]2)=[C:8]([CH:11]=1)[C:9]#[N:10]

Participants

4

Reactant 1

HCID 867045015-Nitro-2-(4-(oxetan-3-yl)piperazin-1-yl)benzonitrile

Product 1

HCID 86704502HCID 86704502, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5-nitro-2-(4-(oxetan-3-yl)piperazin-1-yl)benzonitrile (9.8 g, 1.0 eq, 34.0 mmol) and Pd—C (10% loading, 3,6 g) in EtOH (300 mL) was stirred in a 500 mL round bottom flask. The reaction flask was evacuated under house vacuum and subsequently filled with hydrogen while stirring. This procedure was repeated three times and the reaction mixture was hydrogenated for 3 hours under an H2 balloon. The mixture was filtered through celite and the filter cake was washed with EtOH (2×50 mL). The filtrate was concentrated under vacuum to leave a white solid, which upon high vacuum drying gave 5-amino-2-(4-(oxetan-3-yl)piperazin-1-yl)benzonitrile in 93% yield.

Workup

  1. customThe reaction flask was evacuated under house vacuum
  2. additionsubsequently filled with hydrogen
  3. stirringwhile stirring
  4. filtrationThe mixture was filtered through celite
  5. washthe filter cake was washed with EtOH (2×50 mL)
  6. concentrationThe filtrate was concentrated under vacuum
  7. customto leave a white solid, which upon high vacuum
  8. customdrying

Sources & evidence

ORD record
ord-5af8b77e67b4431da779fee981452691
Source dataset
uspto-grants-2016_04
Patent number
US09321763B2

Reaction notes

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