Acetic Acid → Methyl 4-dipropylaminomethylbenzoate

HRID 348678

Reaction equation

HRID 348678 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH2:12])=[CH:7][CH:6]=1.[C:14]([BH3-])#N.[Na+].[C:18](O)(=O)[CH3:19].[CH:22](=O)[CH2:23][CH3:24]>CO>[CH2:22]([N:12]([CH2:11][C:8]1[CH:9]=[CH:10][C:5]([C:4]([O:3][CH3:2])=[O:13])=[CH:6][CH:7]=1)[CH2:14][CH2:18][CH3:19])[CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 527PropanalHCID 2729253Methyl 4-(aminomethyl)benzoate hydrochlorideHCID 5003444Sodium cyanoborohydride

Product 1

HCID 23079192Methyl 4-dipropylaminomethylbenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In anhydrous methanol (30 ml), 4-aminomethylbenzoic acid methyl ester hydrochloride (1.15 g) was dissolved. Then, the solution was added with sodium cyanoborohydride (1.08 g), acetic acid (5.00 ml), and propionaldehyde (1.03 ml), followed by stirring under a nitrogen atmosphere at room temperature for 1 week. After completion of the reaction, the solvent was distilled off and the residue was then dissolved in chloroform, followed by the addition of a 1 mol/l sodium hydroxide aqueous solution to adjust the solution to pH 9. The solution was subjected to extraction with chloroform. Then, the extract was washed with a saturated aqueous sodium bicarbonate solution and saturated saline solution. The organic layer was dried with anhydrous sodium sulfate and the solvent was then distilled off, thereby obtaining the subject compound (1.49 g) as a colorless liquid.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. dissolutionthe residue was then dissolved in chloroform
  4. additionfollowed by the addition of a 1 mol/l sodium hydroxide aqueous solution
  5. extractionThe solution was subjected to extraction with chloroform
  6. washThen, the extract was washed with a saturated aqueous sodium bicarbonate solution and saturated saline solution
  7. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  8. distillationthe solvent was then distilled off

Sources & evidence

ORD record
ord-24bdc37113cc40ce847d54f5d132812b
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Linked notes

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