Triethylamine → Tyramine hydrochloride

HRID 2058640Notes

Reaction equation

HRID 2058640 reaction equation
[OH-].[Na+].C([N:5]([CH2:8][CH3:9])CC)C.[Cl:10]C([O:13][CH2:14][CH:15]([CH3:17])C)=O.C(Cl)(Cl)Cl.[CH3:22]O.[C:24](O)(=O)[CH3:25]>CN(C)C=O>[ClH:10].[NH2:5][CH2:8][CH2:9][C:22]1[CH:17]=[CH:15][C:14]([OH:13])=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium Hydroxide2×HCID 62365Isobutyl chloroformateHCID 21866353chloroform methanol HOAc

Product 1

HCID 66449Tyramine hydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The product of Example 1, 5.5 mg. (0.014 millimoles) is dissolved in about 2.5 ml. of dimethylformamide and 1.4 ml. of 1 N sodium hydroxide (0.014 millimoles) and 0.2 ml. of triethylamine (0.014 millimoles) are added. The reaction flask is cooled in an ice bath and 0.2 ml. (0.015 millimoles) of isobutyl chloroformate is added. The mixture is stirred gently for 20 min. to allow formation of the mixed anhydride. A solution of 2.4 mg. (0.014 millimoles) of tyramine hydrochloride in dimethylformamide is prepared, neutralized with 1.4 ml. of 1 N sodium hydroxide, and added to the reaction mixture. The reaction mixture is allowed to warm to room temperature with stirring for 60 min. The progress of the amidification reaction is measured by thin-layer chromatography using the solvent system chloroform:methanol:acetic acid (40:10:0.5) in which the starting materials remain near the origin and the product of Formula V migrates with Rf 0.6. After completion of the reaction, the mixture is dried on a rotary evaporator and the residue is resuspended in a small amount of dimethylformamide. Water is added, and the mixture is neutralized with 0.5 M sodium carbonate and the product extracted into ether. The ether phase is dried, the residue dissolved in methanol, and the product purified by thin-layer chromatography using the above solvent system. The major band which appears at Rf 0.6 is eluted from the silica gel with ethanol, concentrated and rechromatographed. The resulting material is used without further purification or characterization for iodination as described below.

Workup

  1. dissolution(0.014 millimoles) is dissolved in about 2.5 ml
  2. temperatureThe reaction flask is cooled in an ice bath
  3. stirringwith stirring for 60 min
  4. customThe progress of the amidification reaction
  5. customAfter completion of the reaction
  6. customthe mixture is dried on a rotary evaporator
  7. additionWater is added
  8. extractionthe product extracted into ether
  9. dry with materialThe ether phase is dried
  10. dissolutionthe residue dissolved in methanol
  11. customthe product purified by thin-layer chromatography
  12. washis eluted from the silica gel with ethanol
  13. concentrationconcentrated
  14. customrechromatographed
  15. customThe resulting material is used without further purification or characterization for iodination

Sources & evidence

ORD record
ord-489089ccfe4149ac9172e65c094680db
Source dataset
uspto-grants-1982_03
Patent number
US04318899

Reaction notes

Loading…