benzyl N-(2-methoxyethyl)-N-(3-pyridylmethyl)carbamate → (2-Methoxyethyl)(pyridin-3-ylmethyl)amine

HRID 581758Notes

Reaction equation

HRID 581758 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)C(=O)OCC1C=CC=CC=1>[Pd].C(O)C>[CH3:1][O:2][CH2:3][CH2:4][NH:5][CH2:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 1

HCID 22112998benzyl N-(2-methoxyethyl)-N-(3-pyridylmethyl)carbamate

Product 1

HCID 4720010(2-Methoxyethyl)(pyridin-3-ylmethyl)amineYield 43.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of benzyl N-(2-methoxyethyl)-N-(3-pyridylmethyl)carbamate (5.4 g) and 10% palladium on carbon (1.0 g) in ethanol (50 ml) was stirred under hydrogen atmosphere for 9 hours. The catalyst was removed by filtration, and the filtrate was concentrated under azeotropic condition with toluene and ethanol. The residue was dissolved in ethanol and diethyl ether was added thereto to give precipitates, which were collected by filtration to give N-(2-methoxyethyl)-N-(3-pyridylmethyl)amine (1.3 g). mp: 134-135° C.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under azeotropic condition with toluene and ethanol
  3. dissolutionThe residue was dissolved in ethanol
  4. additiondiethyl ether was added
  5. customto give
  6. customprecipitates
  7. filtrationwhich were collected by filtration

Sources & evidence

ORD record
ord-36ab5f7774e6493bad4ff2ae16f7f5c9
Source dataset
uspto-grants-1999_07
Patent number
US05922711

Reaction notes

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