HCID 23525787, compound → HCID 23525781, compound

HRID 2415265Notes

Reaction equation

HRID 2415265 reaction equation
[C:1]([O:5][C:6](=[O:23])[N:7]([CH2:21][CH3:22])[CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:23])[N:7]([CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=1)[CH2:21][CH3:22])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 23525787HCID 23525787, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23525781HCID 23525781, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of ethyl-[3-(4-nitrophenoxy)propyl]carbamic acid tert-butyl ester (2.9 g) (from step A above) in ethanol (70 mL) was treated with 10% Pd/C (442 mg) and stirred for 2 hours under 40 psi of hydrogen. The mixture was filtered through a celite pad. The pad was washed with ethanol and the combined solution was evaporated in vacuo to yield [3-(4-aminophenoxy)propyl]-ethyl-carbamic acid tert-butyl ester (2.63 g, 88%). HRMS, Observed: 317.1839; Calcd for M+Na: 317.1835

Workup

  1. filtrationThe mixture was filtered through a celite pad
  2. washThe pad was washed with ethanol
  3. customthe combined solution was evaporated in vacuo

Sources & evidence

ORD record
ord-cd6cf2a8792943938f13cf33885318cc
Source dataset
uspto-grants-2004_11
Patent number
US06818663B2

Reaction notes

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