Potassium Carbonate → N-(2,2-dimethoxyethyl)hexan-1-amine

HRID 1736426Notes

Reaction equation

HRID 1736426 reaction equation
[CH2:1](I)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH3:8][O:9][CH:10]([O:13][CH3:14])[CH2:11][NH2:12].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH3:8][O:9][CH:10]([O:13][CH3:14])[CH2:11][NH:12][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 125271-IodohexaneHCID 89728Aminoacetaldehyde dimethyl acetal

Product 1

HCID 59197986N-(2,2-dimethoxyethyl)hexan-1-amineYield 78.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Hexyl iodide (50 mmol, 7.38 ml) was added to a mixture of 2-amino acetaldehyde dimethyl acetal (100 mmol, 11 ml) and potassium carbonate (50 mmol, 6.9 g) in DMF (10 ml) at 0° C. Stirring was continued for 16 h before diluting with ethyl acetate (200 ml), and filtering the solution through a plug of celite. Concentration in vacuo was follwed by column chromatography (eluant ethyl acetate) to give N-hexyl 2-amino acetaldehyde dimethyl acetal (7.39 g, 78%) as a colourless oil.

Workup

  1. filtrationfiltering the solution through a plug of celite
  2. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-fc3e50c9bb5c4ddc84395079275ba4c6
Source dataset
uspto-grants-1996_07
Patent number
US05541197

Reaction notes

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