2-Methoxyethylamine → HCID 59142758, compound

HRID 1968644Notes

Reaction equation

HRID 1968644 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH2:5].C([O-])([O-])=O.[K+].[K+].Br[CH2:13][CH:14]([O:17][CH3:18])[O:15][CH3:16]>CN(C=O)C.C(OCC)(=O)C>[CH3:16][O:15][CH:14]([O:17][CH3:18])[CH2:13][NH:5][CH2:4][CH2:3][O:2][CH3:1]

Participants

6

Reactant 3

HCID 80182-MethoxyethylamineHCID 11430Potassium CarbonateHCID 816722-Bromo-1,1-dimethoxyethane

Product 1

HCID 59142758HCID 59142758, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-methoxyethanamine (100 mg, 1.33 mmol) in DMF (2 mL) was added K2CO3 (276 mg, 1.99 mmol) and 2-bromo-1,1-dimethoxyethane (236 mg, 1.39 mmol). The mixture was stirred at 80° C. for 3 h. After cooled to room temperature, the reaction mixture was diluted with ethyl acetate and washed with water and brine. The organic layer was concentrated to give 2,2-dimethoxy-N-(2-methoxyethyl)ethanamine as a yellow oil in 91% yield and used in the next step without purification.

Workup

  1. temperatureAfter cooled to room temperature
  2. washwashed with water and brine
  3. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-a7503c3b714045b6aab6a9b6e611b5e8
Source dataset
uspto-grants-2013_04
Patent number
US08426430B2

Reaction notes

Loading…