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

HRID 16484Notes

Reaction equation

HRID 16484 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-3d2009b0f75644f2850e03cd9589d6c2
Source dataset
uspto-grants-2010_06
Patent number
US07737145B2

Reaction notes

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