Ethanol → 5-Amino-2-(4-isopropylpiperazin-1-yl)benzonitrile

HRID 633450Notes

Reaction equation

HRID 633450 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][C:11]=2[C:12]#[N:13])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].CCO.CC1C=C2N=C3C(=NC(NC3=O)=O)N(C[C@H](O)[C@H](O)[C@H](O)CO)C2=CC=1C>O.[Pd]>[NH2:18][C:15]1[CH:16]=[CH:17][C:10]([N:7]2[CH2:8][CH2:9][N:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][CH2:6]2)=[C:11]([CH:14]=1)[C:12]#[N:13]

Participants

6

Reactant 3

HCID 702EthanolHCID 493570RiboflavinHCID 339954542-(4-Isopropylpiperazin-1-yl)-5-nitrobenzonitrile

Product 1

HCID 612969195-Amino-2-(4-isopropylpiperazin-1-yl)benzonitrileYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A round-bottom flask was charged with 2-(4-isopropylpiperazin-1-yl)-5-nitrobenzonitrile (1.76 g, 6.42 mmol), EtOH (65 mL), and 10% Pd/C (50% in water, Degussa type E101; 355 mg, 20 wt % by weight of the starting nitro compound). The flask was sealed with a rubber septum, degassed, and back-filled with H2 (×3) from a balloon filled with H2. The reaction was stirred for 2 h using a H2 filled balloon. The reaction mixture was filtered through a pad of celite, and the pad of celite was rinsed with MeOH. The filtrate was evaporated to dryness, and the product dried in vacuo to provide 5-amino-2-(4-isopropylpiperazin-1-yl)benzonitrile (1.49 g, 95% yield) as a yellow solid that was used without further purification.

Workup

  1. customThe flask was sealed with a rubber septum
  2. customdegassed
  3. additionback-filled with H2 (×3) from a balloon
  4. additionfilled with H2
  5. filtrationThe reaction mixture was filtered through a pad of celite
  6. washthe pad of celite was rinsed with MeOH
  7. customThe filtrate was evaporated to dryness
  8. customthe product dried in vacuo

Sources & evidence

ORD record
ord-61cce0cfdeb84e549f38c981fc053a44
Source dataset
uspto-grants-2016_04
Patent number
US09321763B2

Reaction notes

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