Diisopropyl Ether → tert-butyl N-[(4-aminophenyl)methyl]-N-methylcarbamate

HRID 1385501Notes

Reaction equation

HRID 1385501 reaction equation
[C:1]([O:5][C:6](=[O:19])[N:7]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[H][H].C(OC(C)C)(C)C>[Pd].CCOC(C)=O>[C:1]([O:5][C:6](=[O:19])[N:7]([CH2:9][C:10]1[CH:11]=[CH:12][C:13]([NH2:16])=[CH:14][CH:15]=1)[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 7914Diisopropyl EtherHCID 11579844Tert-butyl N-methyl-N-[(4-nitrophenyl)methyl]carbamateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 11637262tert-butyl N-[(4-aminophenyl)methyl]-N-methylcarbamateYield 66.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A Parr bottle was charged with (4-nitrobenzyl)-methy-carbarnic acid tert-butyl ester (30.0 g, 113 mmol), 150 mL EtOAc, and 10% Pd/C (3.0 g, 10 wt %), and shaken under 40 psi hydrogen for 90 min. When hydrogen uptake ceased, the reaction vessel was purged with nitrogen, filtered through celite, and concentrated to provide a tan solid, which was granulated with 300 mL of isopropyl ether to provide the title compound as an off-white solid (17.7 g in two crops, 75 mmol, 66% yield):

Workup

  1. customthe reaction vessel was purged with nitrogen
  2. filtrationfiltered through celite
  3. concentrationconcentrated
  4. customto provide a tan solid, which

Sources & evidence

ORD record
ord-c75b805b8a3b4ac587be59af8899b4e9
Source dataset
uspto-grants-2001_07
Patent number
US06262272B1

Reaction notes

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