Methanol → 1-Boc-4-(5-amino-6-methyl-2-pyridinyl)piperazine

HRID 1993635Notes

Reaction equation

HRID 1993635 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[C:16]([CH3:23])[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.[H][H]>C1COCC1.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([CH3:23])[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 887MethanolHCID 685380371-Boc-4-(6-methyl-5-nitro-2-pyridinyl)-piperazineHCID 178418361HCID 178418361, compound

Product 1

HCID 591344511-Boc-4-(5-amino-6-methyl-2-pyridinyl)piperazineYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Mix a slurry of 4-(6-methyl-5-nitro-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester (46.00 g, 142.7 mmol) in THF (750 mL) at room temperature with Pd/C (5% Aldrich, 3.04 g, 1.43 mmol) then place under a hydrogen atmosphere (Parr shaker, 40-45 psi) for 6 hours. Add MeOH (250 mL), and subject the slurry to an atmosphere of hydrogen for 4 hours at room temperature. Add additional catalyst (3.04 g), then place the mixture under hydrogen for 7 hours. Filter the mixture through a pad of Celite 521®, washing with THF and MeOH then concentrate under reduced pressure to provide the title compound a pale pink solid. (41.58 g, 99% yield, MS(ES+): m/z=293 [M+H]).

Workup

  1. customfor 6 hours
  2. customfor 4 hours
  3. customat room temperature
  4. filtrationFilter the mixture through a pad of Celite 521®
  5. washwashing with THF and MeOH
  6. concentrationthen concentrate under reduced pressure

Sources & evidence

ORD record
ord-c34a8db5a40047efbbf4d91a17a0178e
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

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