tert-Butyl 4-((4-nitrobenzo[d]oxazol-2-yl)methyl)piperazine-1-carboxylate → tert-Butyl 4-((4-aminobenzo[d]oxazol-2-yl)methyl)piperazine-1-carboxylate

HRID 2237424Notes

Reaction equation

HRID 2237424 reaction equation
[N+:1]([C:4]1[C:9]2[N:10]=[C:11]([CH2:13][N:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]3)[O:12][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O.[H][H]>CO.[Pd]>[NH2:1][C:4]1[C:9]2[N:10]=[C:11]([CH2:13][N:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]3)[O:12][C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 59302730tert-Butyl 4-((4-nitrobenzo[d]oxazol-2-yl)methyl)piperazine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 59302726tert-Butyl 4-((4-aminobenzo[d]oxazol-2-yl)methyl)piperazine-1-carboxylateYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 4-((4-nitrobenzo[d]oxazol-2-yl)methyl)piperazine-1-carboxylate (5.97 g, 16.6 mmol, 1.0 equiv) in MeOH (49 mL) was added Pd/C (10% Pd, wet, 2.99 g). The resulting suspension was fixed with a hydrogen balloon and sparged with hydrogen while stirring was maintained. After 1 h, the mixture was filtered through a pad of celite and concentrated in vacuo to provide the title compound as an off-white solid (5.0 g, 91%).

Workup

  1. customsparged with hydrogen
  2. temperaturewas maintained
  3. filtrationthe mixture was filtered through a pad of celite
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-719fc040729845df88ebb99c00f3ca2c
Source dataset
uspto-grants-2010_05
Patent number
US07718657B2

Reaction notes

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