Triethylamine → Methyl 3-{[[2-(diethylamino)ethyl](methyl)amino]methyl}-5-methylbenzoate

HRID 348920

Reaction equation

HRID 348920 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([CH3:13])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].C(N(CC)CC)C.CS(Cl)(=O)=O.[CH2:26]([N:28]([CH2:33][CH3:34])[CH2:29][CH2:30][NH:31][CH3:32])[CH3:27]>C(Cl)Cl>[CH2:26]([N:28]([CH2:33][CH3:34])[CH2:29][CH2:30][N:31]([CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([CH3:13])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])[CH3:32])[CH3:27]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 660341,2-Ethanediamine, N1,N1-diethyl-N2-methyl-HCID 21086184Methyl 3-(hydroxymethyl)-5-methylbenzoate

Product 1

HCID 21086144Methyl 3-{[[2-(diethylamino)ethyl](methyl)amino]methyl}-5-methylbenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cold, stirred solution of methyl 3-(hydroxymethyl)-5-methylbenzoate (200 mg, 1.19 mmol) and triethylamine (241 mg, 2.38 mmol) in methylene chloride (5 mL) is added methanesulfonyl chloride (191 mg, 1.67 mmol). The reaction mixture is stirred for 15 min, the precipitate that formed is removed by filtration, and N,N-diethyl-N′-methylethylenediamine (465 mg, 3.57 mmol) was added. The reaction mixture is stirred at room temperature for 2 h and then concentrated under reduced pressure. Purification by flash column chromatography (silica, 9:1 chloroform/methanol) gives the title compound. 1H NMR (300 MHz, CDCl3) δ 8.02 (s, 2H), 7.33 (s, 1H), 3.56 (s, 3H), 3.48 (s, 2H), 2.95 (m, 4H), 2.75 (m, 4H), 2.41 (s, 3H), 2.31 (s, 3H), 1.21 (m, 6H).

Workup

  1. customthe precipitate that formed
  2. additionwas added
  3. stirringThe reaction mixture is stirred at room temperature for 2 h
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash column chromatography (silica, 9:1 chloroform/methanol)

Sources & evidence

ORD record
ord-d22768786d2541f198156eeb45ac8706
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Linked notes

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