Benzyl 4-propionylpiperazine-1-carboxylate → 1-(Piperazin-1-yl)propan-1-one

HRID 922380

Reaction equation

HRID 922380 reaction equation
[C:1]([N:5]1[CH2:10][CH2:9][N:8](C(OCC2C=CC=CC=2)=O)[CH2:7][CH2:6]1)(=[O:4])[CH2:2][CH3:3].[H][H]>[Pd].C(O)C>[N:5]1([C:1](=[O:4])[CH2:2][CH3:3])[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1

Participants

5

Reactant 2

HCID 22596214Benzyl 4-propionylpiperazine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 38443751-(Piperazin-1-yl)propan-1-oneYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A Parr shaker bottle was charged with a suspension of benzyl 4-propionylpiperazine-1-carboxylate (16), 10% palladium on carbon, 50% wet (900 mg) and absolute ethanol (100 mL). The Parr bottle was filled with 20 psi of hydrogen and shook for 3 h at rt. The resulting suspension was filtered through Celite and concentrated to yield the title compound (4.31 g, 93%) as a clear, colorless oil: 1H NMR (500 MHz, CDCl3) δ 3.75-3.63 (m, 2H), 3.48-3.42 (m, 2H), 2.87-2.80 (m, 4H), 2.34 (q, J=7.5 Hz, 2H), 1.98 (br s, 1H), 1.15 (t, J=7.5 Hz, 3H).

Workup

  1. filtrationThe resulting suspension was filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-64636ef78e1d454c98d7a2960ae70958
Source dataset
uspto-grants-2016_03
Patent number
US09278940B2

Linked notes

Loading…