Triethylamine → 4-(2-Dimethylaminoethylaminomethyl)benzoic acid benzyl ester

HRID 217639Notes

Reaction equation

HRID 217639 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH2:5].[CH2:7]([O:14][C:15](=[O:28])[C:16]1[CH:21]=[CH:20][C:19]([CH2:22]OS(C)(=O)=O)=[CH:18][CH:17]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>CN(C=O)C>[CH2:7]([O:14][C:15](=[O:28])[C:16]1[CH:17]=[CH:18][C:19]([CH2:22][NH:5][CH2:4][CH2:3][N:2]([CH3:6])[CH3:1])=[CH:20][CH:21]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 66053N,N-DimethylethylenediamineHCID 516892Sodium BicarbonateHCID 580012134-Methanesulfonyloxymethylbenzoic acid benzyl ester

Product 1

HCID 588900084-(2-Dimethylaminoethylaminomethyl)benzoic acid benzyl esterYield 53.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N-Dimethylethylenediamine (0.90 mL, 8.2 mmol) was added to a solution of 4-methanesulfonyloxymethylbenzoic acid benzyl ester (Reference Compound No. 8-1, 2.3 g, 7.2 mmol) and triethylamine (3.0 mL, 22 mmol) in DMF (10 mL), and then the reaction mixture was stirred at room temperature for 2 hours. Saturated aqueous sodium hydrogen carbonate solution (0.15 L) was added to the reaction solution, and the whole was extracted with chloroform (0.10 L) three times. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure to give 1.2 g of mixture including the title reference compound as yellow oil.

Workup

  1. extractionthe whole was extracted with chloroform (0.10 L) three times
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-26ca5ad5a2cf4807a0955f26029bcab6
Source dataset
uspto-grants-2012_06
Patent number
US08198271B2

Reaction notes

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