Acetic Acid → HCID 16781125, compound

HRID 131263Notes

Reaction equation

HRID 131263 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)=O.[CH3:13][N:14]([CH3:18])[CH2:15][CH2:16][NH2:17].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:13][N:14]([CH3:18])[CH2:15][CH2:16][NH:17][CH2:1][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 15294Methyl 4-FormylbenzoateHCID 66053N,N-DimethylethylenediamineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 16781125HCID 16781125, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-formylbenzoate (25 g) in methylene chloride (250 mL) is added successively N,N-dimethylethylenediamine (67 g), acetic acid (87 mL), and sodium triacetoxyborohydride (50.6 g). The mixture is stirred at room temperature overnight. The reaction mixture is concentrated in vacuo and to the residue is added a saturated potassium carbonate solution. The mixture is extracted with ethyl acetate, and the organic layer is dried over anhydrous sodium sulfate and concentrated in vacuo to give methyl 4-[[[2-(dimethylamino)ethyl]amino]methyl]-benzoate (31.9 g, yield; 89%) as a colorless oil. MS (APCI) m/z: 237 [M+H]+

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo and to the residue
  2. additionis added a saturated potassium carbonate solution
  3. extractionThe mixture is extracted with ethyl acetate
  4. dry with materialthe organic layer is dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a69e47c677e740c8ae96d47ffcbaa79d
Source dataset
uspto-grants-2008_06
Patent number
US07384952B2

Reaction notes

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