Hydrochloric Acid → Dopamine

HRID 1045270Notes

Reaction equation

HRID 1045270 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]1[CH:12]=[CH:11][C:9]([OH:10])=[C:7]([OH:8])[CH:6]=1.[OH-].[Na+].Cl>O>[NH2:2][CH2:3][CH2:4][C:5]1[CH:12]=[CH:11][C:9]([OH:10])=[C:7]([OH:8])[CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 65340Dopamine Hydrochloride

Product 1

HCID 681Dopamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dopamine hydrochloride (7.4 mg, 0.0194 mmol) and mPEG (5 kDa)-dopamine (100 mg, 0.0194 mmol) were dissolved in 7 mL water. 1 mL of 1N sodium hydroxid solution was added and the mixture was stirred for 17 hours at room temperature. The resulting solution was acidified with 1 mL of 2 N HCl, filtered and dialyzed against ultrapure water. The final solution was lyophilized to give 100 mg poly(mPEGdopamin/dopamine). The ratios between dopamine and PEG dopamine can be varied. The reaction conditions lead to a ring closure by a nucleophilic attack of the amine/amide which is proofed by the loss of aromatic protons in the 1H-NMR spectrum.

Workup

  1. filtrationfiltered
  2. customdialyzed against ultrapure water

Sources & evidence

ORD record
ord-b9aa1333f8c64ef98276d15533093f8e
Source dataset
uspto-grants-2013_10
Patent number
US08568872B2

Reaction notes

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