Methanol → tert-Butyl 4-(5-aminopyridin-2-yl)piperazine-1-carboxylate

HRID 1993637Notes

Reaction equation

HRID 1993637 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)=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.[H][H]>[Pd].CCOC(C)=O>[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])=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 887MethanolHCID 16217943tert-Butyl 4-(5-nitropyridin-2-yl)piperazine-1-carboxylateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 17999304tert-Butyl 4-(5-aminopyridin-2-yl)piperazine-1-carboxylateYield 98.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

Place 4-(5-nitro-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester (1.14 g, 3.70 mmol) in 1:1 EtOAc:MeOH (20 mL). Add 10% Pd on carbon using EtOAc (5 mL). Purge the reaction and then add hydrogen. Repeat the purge/fill cycle twice and place the reaction under a balloon of hydrogen and stir at room temperature for 20 hours. Filter the reaction through a pad of Celite® and wash the filter cake with EtOAc. Collect the filtrate and concentrate under reduced pressure to yield 1.01 g (98%) of the title compound. MS(ES): m/z=279 [M+H].

Workup

  1. customPurge
  2. customthe reaction
  3. filtrationFilter
  4. customthe reaction through a pad of Celite®
  5. washwash the filter cake with EtOAc
  6. customCollect the filtrate
  7. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-63cc4d8a1433408dbf10fc95a62f7a9b
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

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