HCID 57664371, compound → HCID 57664372, compound

HRID 1011268Notes

Reaction equation

HRID 1011268 reaction equation
[CH:1]1([N:5]2[CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=3)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1>CCO.[Pd]>[CH:1]1([N:5]2[CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=3)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 57664371HCID 57664371, compound

Product 1

HCID 57664372HCID 57664372, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a 250-mL round bottom flasked is added 10% Pd/C (100 mg). The flask was sealed with a septum, and flushed with a slow stream of N2. 1-Cyclobutyl-4-(4-nitrophenyl)piperazine (1 g, 3.83 mmol) was dissolved in EtOH (30 mL) and transferred via syringe into the flask. The flask is again flushed with N2 and then it is fitted with a balloon of hydrogen. An outlet needle is inserted through the septum and the flask is flushed with hydrogen before the outlet needle is removed. The resulting slurry is stirred vigorously under the H2 atmosphere at rt. After 24 h the yellow color of the solution dissipates and the hydrogen balloon is removed. The flask is flushed with nitrogen, DCM (10 mL) is added to the reaction mixture, and the resulting slurry is stirred at rt for 1.5 h. The reaction is filtered through a filtration tube packed with a short column of Celite, the Celite washed with DCM (2×20 mL), and the combined filtrate evaporated to dryness on a rotary evaporator. The product is air dried for 48 h and then dried under vacuum for 2 h to provide crude 4-(4-cyclobutylpiperazin-1-yl)aniline (0.87 g, 98% recovery, 100% purity as determined by LC/MS analysis @ UV 254 nm detection). The crude product was used in the next step without further purification. LCMS-ESI (m/z): calcd for C14H21N3, 231; [M+H]+ found, 232.

Workup

  1. customThe flask was sealed with a septum
  2. customflushed with a slow stream of N2
  3. customtransferred via syringe into the flask
  4. customThe flask is again flushed with N2
  5. customit is fitted with a balloon of hydrogen
  6. customAn outlet needle is inserted through the septum
  7. customthe flask is flushed with hydrogen before the outlet needle
  8. customis removed
  9. customthe hydrogen balloon is removed
  10. customThe flask is flushed with nitrogen, DCM (10 mL)
  11. additionis added to the reaction mixture
  12. stirringthe resulting slurry is stirred at rt for 1.5 h
  13. filtrationThe reaction is filtered through a filtration tube
  14. washthe Celite washed with DCM (2×20 mL)
  15. customthe combined filtrate evaporated to dryness on a rotary evaporator
  16. customdried for 48 h
  17. customdried under vacuum for 2 h

Sources & evidence

ORD record
ord-ea511265a7b74e318947626858eca8e8
Source dataset
uspto-grants-2011_07
Patent number
US07977352B2

Reaction notes

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