Bis(2-Methoxyethyl)amine → Benzyl (bis(2-methoxyethyl)amino)acetate

HRID 583934Notes

Reaction equation

HRID 583934 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].[CH3:13][O:14][CH2:15][CH2:16][NH:17][CH2:18][CH2:19][O:20][CH3:21]>ClCCl>[CH3:13][O:14][CH2:15][CH2:16][N:17]([CH2:2][C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4])[CH2:18][CH2:19][O:20][CH3:21]

Participants

4

Reactant 2

HCID 2383Bis(2-Methoxyethyl)amineHCID 62576Benzyl bromoacetate

Product 1

HCID 53622886Benzyl (bis(2-methoxyethyl)amino)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of benzyl bromoacetate (28.9 g; 96.7 mmol) in dichloromethane (100 mL) at room temperature was treated with 2-methoxy-N-(2-methoxyethyl)ethanamine (40.6 g; 305 mmol), stirred for 30 minutes, diluted with dichloromethane, washed sequentially with saturated NH4Cl, water, and brine, dried (Na2SO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 40% diethyl ether/dichloromethane to provide the desired product.

Workup

  1. washwashed sequentially with saturated NH4Cl, water, and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash column chromatography on silica gel with 40% diethyl ether/dichloromethane

Sources & evidence

ORD record
ord-28ce82a4d2fe4d408bbb8d6f9863ccc6
Source dataset
uspto-grants-2005_08
Patent number
US06924304B2

Reaction notes

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