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

HRID 1059845Notes

Reaction equation

HRID 1059845 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-7984da16fe1a45a7a9f3d0e0f84fca93
Source dataset
uspto-grants-2003_02
Patent number
US06521658B1

Reaction notes

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