Ammonium formate → Tert-butyl 4-aminophenethylcarbamate

HRID 1518179Notes

Reaction equation

HRID 1518179 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>C(O)C.[Pd].O>[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 10264884Tert-butyl N-[2-(4-nitrophenyl)ethyl]carbamate

Product 1

HCID 382207Tert-butyl 4-aminophenethylcarbamateYield 81.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of [2-(4-nitro-phenyl)-ethyl]-carbamicacid tert-butyl ester (18.7 g, 70.30 mmol) in ethanol (200 ml) a slurry of 10% palladium on charcoal (2 g) in water (10 ml) was added. At 80° C. ammonium formate (44.3 g, 703 mmol) in water (90 ml) was added slowly. After complete addition the mixture was stirred at 80° C. for 1 h. The mixture was allowed to come to room temperature, filtered and concentrated in vacuo. The residue was diluted with water and extracted twice with dichloromethane. The combined organic layers were washed with water, dried over MgSO4, filtered and the solvent evaporated under reduced pressure to give the product as a yellow oil (13.5 g, 81%).

Workup

  1. additionAfter complete addition the mixture
  2. customto come to room temperature
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. additionThe residue was diluted with water
  6. extractionextracted twice with dichloromethane
  7. washThe combined organic layers were washed with water
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-f946030c8a794c279633d0c3a67c3035
Source dataset
uspto-grants-2012_07
Patent number
US08232426B2

Reaction notes

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