Acetic Acid → HCID 13455620, compound

HRID 348676Notes

Reaction equation

HRID 348676 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[C:11]([BH3-])#N.[Na+].[C:15](O)(=O)[CH3:16].[CH:19](=O)[CH2:20][CH3:21]>CO>[CH2:19]([N:1]([CH2:11][CH2:15][CH3:16])[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)[CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 527PropanalHCID 5610TyramineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 13455620HCID 13455620, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Tyramine (manufactured by Tokyo Kasei Kogyo Co., Ltd.) (591 mg) was dissolved in anhydrous methanol (12 ml) and then added with sodium cyanoborohydride (812 mg), acetic acid (5.00 ml), and propionaldehyde (777 μl), followed by stirring at room temperature under a nitrogen atmosphere for 2 days. After completion of the reaction, the solvent was distilled off. Then, the residue was dissolved in diethyl ether and then stirred after the addition of distilled water. The solution was subjected to extraction with diethyl ether and the extract was then washed with distilled water and a saturated aqueous ammonium chloride solution. The organic layer was dried with anhydrous sodium sulfate and the solvent was then distilled off, thereby obtaining the subject compound (412 mg) as a dark brown liquid.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. dissolutionThen, the residue was dissolved in diethyl ether
  4. stirringstirred
  5. additionafter the addition of distilled water
  6. extractionThe solution was subjected to extraction with diethyl ether
  7. washthe extract was then washed with distilled water
  8. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  9. distillationthe solvent was then distilled off

Sources & evidence

ORD record
ord-caec5fbbf4dd434688025f2cf809e2db
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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