Reaction #710550

Reaction equation

3-hydroxytyramine

Gluconolactone

triethylamine

gluconolactone

→

dopamine gluconamide

Yield 48.6%

Solvents

methanol

Conditions

Workup

1. 1
   workup.DISSOLUTIONto dissolve
2. 2
   workup.DISSOLUTIONWhen the solid was dissolved
3. 3
   workup.STIRRINGthe solution was stirred for an additional 10 minutes
4. 4
   workup.DISSOLUTIONto dissolve
5. 5
   workup.STIRRINGThe reaction mixture was stirred in the dark for about 2 hrs
6. 6
   FiltrationThe white solid precipitant was collected by filtration
7. 7
   Washwashed with methanol (5 mL)
8. 8
   Otherdried in vacuo for 6 hrs

Procedure

Gluconolactone (1.9 gm, 10.5 mmol) and triethylamine (TEA; 1.1 gm, 10.5 mmol) were added to methanol (25 mL) in a 100 mL round bottom flask with stirring. The gluconolactone was allowed to dissolve. When the solid was dissolved, the solution was stirred for an additional 10 minutes and then 3-hydroxytyramine (2.0 gm, 10.5 mmol) was added slowly, i.e., allowing it to dissolve. The reaction mixture was stirred in the dark for about 2 hrs. during which time a white solid precipitant appeared. The white solid precipitant was collected by filtration, washed with methanol (5 mL) and dried in vacuo for 6 hrs. to give dopamine gluconamide (1.69 gm, 5.10 mmol, 48.6% yield). Melting point of the synthesis product was 154-155° C. Predicted: C14H21N1 (331.32): C, −50.75%; H, −6.39%; N, −4.23%; analysis results of synthetic product: C, 50.65; H, 6.63; N, 4.44.

Source