HCID 131730033, compound → tert-Butyl 4-(3-aminopyridin-4-yl)piperazine-1-carboxylate

HRID 526051Notes

Reaction equation

HRID 526051 reaction equation
[N+]([CH:4]1[N:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8][CH2:7][N:6]([C:17]2[CH:22]=[CH:21]C=CN=2)[CH2:5]1)([O-])=O>C(Cl)Cl.[Pd]>[C:13]([O:12][C:10]([N:9]1[CH2:4][CH2:5][N:6]([C:17]2[CH:22]=[CH:21][N:6]=[CH:5][C:4]=2[NH2:9])[CH2:7][CH2:8]1)=[O:11])([CH3:14])([CH3:15])[CH3:16]

Participants

4

Reactant 1

HCID 131730033HCID 131730033, compound

Product 1

HCID 43462405tert-Butyl 4-(3-aminopyridin-4-yl)piperazine-1-carboxylateYield 197.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

Step 2) 3-Nitro-4-boc piperizinyl pyridine 3 (37 g, 0.12 mol) was dissolved in DCM (500 mL). The resulting solution was subjected Pd/C (10%, 14.8 g) and was kept under hydrogen atmosphere at room temperature. Overnight stirring and monitored the reaction progress until the reaction is complete. The reaction solution was filtered through celite, washed with DCM/MeOH and concentrated to give the product, 4-(3-Amino-pyridin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester 4 (33 g) in the yield of around 99%.

Workup

  1. customwas kept under hydrogen atmosphere at room temperature
  2. filtrationThe reaction solution was filtered through celite
  3. washwashed with DCM/MeOH
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e3fe15e1946b48e9bee8a5bc37240931
Source dataset
uspto-grants-2016_05
Patent number
US09345705B2

Reaction notes

Loading…