Tert-butyl 4-(3-nitrophenethyl)piperazine-1-carboxylate → Tert-butyl 4-(3-aminophenethyl)piperazine-1-carboxylate

HRID 2093435Notes

Reaction equation

HRID 2093435 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:22]=[CH:23][CH:24]=1)[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1)([O-])=O.[H][H]>CO.[Pd].[OH-].[OH-].[Pd+2]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:22]=[CH:23][CH:24]=1)[CH2:7][CH2:8][N:9]1[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:20])([CH3:21])[CH3:19])=[O:16])[CH2:13][CH2:14]1

Participants

6

Reactant 2

HCID 57597097Tert-butyl 4-(3-nitrophenethyl)piperazine-1-carboxylate2×HCID 178418361HCID 178418361, compound

Product 1

HCID 57597088Tert-butyl 4-(3-aminophenethyl)piperazine-1-carboxylateYield 63%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A Parr glass liner was charged with tert-butyl 4-(3-nitrophenethyl)piper-azine-1-carboxylate (7C, 1.0 eq) and methanol (about 0.2 M 7C in MeOH). To this solution was added a slurry of 12.5 wt eq of 10% Pd/C in methanol. The reaction mixture was sealed in a Parr hydrogenation vessel and subjected to 3 pressurization/venting cycles with H2. The reaction mixture was allowed to proceed at room temperature and 45 psi H2 for 2.5 h. The reaction mixture was then charged with 12.5 wt eq of Pd(OH)2/C and the vessel was repressurized with hydrogen (45 psi). After 1 hr, the reaction mixture was filtered through a pad of diatomaceous earth, the diatomaceous earth washed with MeOH, and the combine organic layers concentrated in vacuo to provide the desired tert-butyl 4-(3-aminophenethyl)piperazine-1-carboxylate (7D, 63%), which was used without further purification.

Workup

  1. customThe reaction mixture was sealed in a Parr hydrogenation vessel
  2. customto proceed at room temperature
  3. waitAfter 1 hr
  4. filtrationthe reaction mixture was filtered through a pad of diatomaceous earth
  5. washthe diatomaceous earth washed with MeOH
  6. concentrationthe combine organic layers concentrated in vacuo

Sources & evidence

ORD record
ord-656e8606ce074946832595f0d6755cb9
Source dataset
uspto-grants-2013_05
Patent number
US08445495B2

Reaction notes

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