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

HRID 658036
Notes
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Reaction equation

HRID 658036 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6228
Dimethylformamide
Solvent

Procedure

N,N-Dimethylethylenediamine (0.87 mL, 7.9 mmol) was added to a solution of 4-methanesulfonyloxymethylbenzoic acid benzyl ester (Reference Compound No. 7-1, 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 (150 mL) was added thereto, and then the whole was extracted with chloroform (100 mL) 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 a mixture, which contains the title reference compound as yellow oil.

Workup

  1. extractionthe whole was extracted with chloroform (100 mL) 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-72c8b16a235448f8a9cbd27927aaea2d
Source dataset
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08076332B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes