Benzyl 4-(2-(benzyloxy)pyridin-3-yl)piperazine-1-carboxylate → 3-piperazin-1-ylpyridin-2(1H)-one

HRID 1804620Notes

Reaction equation

HRID 1804620 reaction equation
C([O:8][C:9]1[C:14]([N:15]2[CH2:20][CH2:19][N:18](C(OCC3C=CC=CC=3)=O)[CH2:17][CH2:16]2)=[CH:13][CH:12]=[CH:11][N:10]=1)C1C=CC=CC=1>[Pd].CO>[N:15]1([C:14]2[C:9](=[O:8])[NH:10][CH:11]=[CH:12][CH:13]=2)[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]1

Participants

4

Reactant 1

HCID 67060675Benzyl 4-(2-(benzyloxy)pyridin-3-yl)piperazine-1-carboxylate

Product 1

HCID 679720663-piperazin-1-ylpyridin-2(1H)-oneYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a 10 mL round bottomed flask was added 10 mg (0.009 mmol) of 10% palladium on activated carbon which was then flushed with nitrogen. Next, a solution of 0.090 (0.22 mmol) of benzyl 4-[2-(benzyloxy)pyridin-3-yl]piperazine-1-carboxylate from Step A above in 4 mL of methanol was added and the resulting mixture was placed under an atmosphere of hydrogen gas at atmospheric pressure for 3 h. The reaction was then flushed with nitrogen and filtered through a pad of Celite®. The pad was washed with methanol and the combined organics were evaporated to dryness to afford the title compound as a clear gum (0.035 g, 88%). LC-MS: m/z (ES) 180.1 (MH)+.

Workup

  1. customwas then flushed with nitrogen
  2. customThe reaction was then flushed with nitrogen
  3. filtrationfiltered through a pad of Celite®
  4. washThe pad was washed with methanol
  5. customthe combined organics were evaporated to dryness

Sources & evidence

ORD record
ord-c2f15bd675e64faf960ff61965aa5eb8
Source dataset
uspto-grants-2013_01
Patent number
US08354403B2

Reaction notes

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