Dopamine → HCID 67389189, compound

HRID 570113Notes

Reaction equation

HRID 570113 reaction equation
[CH2:1]([OH:12])[C@H:2]1[O:8][C:6](=[O:7])[C@H:5]([OH:9])[C@@H:4]([OH:10])[C@@H:3]1[OH:11].C([N:15](CC)CC)C.[OH:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][C:29]=1[OH:30])[CH2:24][CH2:25][NH2:26]>CO>[O:7]=[C:6]([NH2:15])[C@@H:5]([C@H:4]([C@@H:3]([C@@H:2]([CH2:1][OH:12])[OH:8])[OH:11])[OH:10])[OH:9].[NH2:26][CH2:25][CH2:24][C:23]1[CH:27]=[CH:28][C:29]([OH:30])=[C:21]([OH:20])[CH:22]=1

Participants

5

Reactant 3

HCID 681DopamineHCID 7027delta-Gluconolactone2×HCID 8471Triethylamine

Product 1

HCID 67389189HCID 67389189, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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, 4.444.

Workup

  1. dissolutionto dissolve
  2. dissolutionWhen the solid was dissolved
  3. stirringthe solution was stirred for an additional 10 minutes
  4. dissolutionto dissolve
  5. stirringThe reaction mixture was stirred in the dark for about 2 hrs
  6. filtrationThe white solid precipitant was collected by filtration
  7. washwashed with methanol (5 mL)
  8. customdried in vacuo for 6 hrs

Sources & evidence

ORD record
ord-986de342394c4841907bc1253c7aa55b
Source dataset
uspto-grants-2015_05
Patent number
US09023818B2

Reaction notes

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