N,N'-Dimethylethylenediamine → Methyl 4-((methyl(2-(methylamino)ethyl)amino)methyl)benzoate

HRID 1046293Notes

Reaction equation

HRID 1046293 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.[CH3:13][NH:14][CH2:15][CH2:16][NH:17][CH3:18].C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH3:13][N:14]([CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)[CH2:15][CH2:16][NH:17][CH3:18]

Participants

6

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 8471TriethylamineHCID 256687Methyl 4-(bromomethyl)benzoateHCID 516892Sodium Bicarbonate

Product 1

HCID 64081796Methyl 4-((methyl(2-(methylamino)ethyl)amino)methyl)benzoateYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 4-(bromomethyl)benzoate (2 g, 8.73 mmol) and N,N′-dimethylethan-1,2-diamine (7.5 mL, 70 mmol) was heated with triethylamine (9.8 mL, 70 mmol) in tetrahydrofuran (80 mL) to reflux for two hours. After cooling, the mixture was treated with saturated sodium bicarbonate solution. The mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. Flash chromatography gave 1.28 g of methyl 4-[(methyl(2-(methylamino)ethyl)amino)methyl]benzoate, 1H NMR (300 MHz, CD3OD) δ 7.97 (d, 2H), 7.45 (d, 2H), 3.59 (s, 2H), 2.67 (m, 2H), 2.54 (m, 2H), 2.35 (s, 3H), 2.22 (s, 3H) ppm.

Workup

  1. temperatureto reflux for two hours
  2. temperatureAfter cooling
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-197106172a2a4b758b2e55b3cdc1bfee
Source dataset
uspto-grants-2013_10
Patent number
US08569303B2

Reaction notes

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