Triethylamine → Dopamine

HRID 1661840Notes

Reaction equation

HRID 1661840 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.Cl.[NH2:36][CH2:37][CH2:38][C:39]1[CH:46]=[CH:45][C:43]([OH:44])=[C:41]([OH:42])[CH:40]=1.CCN(CC)CC>C(Cl)(Cl)Cl.CN(C=O)C.C(OCC)C>[NH2:36][CH2:37][CH2:38][C:39]1[CH:46]=[CH:45][C:43]([OH:44])=[C:41]([OH:42])[CH:40]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65340Dopamine HydrochlorideHCID 757711-HydroxybenzotriazoleHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 681Dopamine

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

8 g of p(EG600DMPA-SA) (10 mmol —COOH) was dissolved in 20 mL of chloroform and 10 mL of DMF. 3.8 g of HBTU (26 mmol), 1.35 g of HOBt (10 mmol), 2.8 g of dopamine HCl (15 mmol), and 3.64 mL of Et3N (26 mmol) were added and the reaction mixture was stirred for an hour. The mixture was added to 400 mL of ethyl ether and the precipitated polymer was further purified by dialyzing using 3500 MWCO dialysis tubing in deionized water for 24 hrs. After lyophilization, 600 mg of PEE-9 was obtained (GPC-LS: Mw=15,000, PD=4.8; UV-vis: 1.0±0.053 μmmol dopamine/mg polymer, 16±0.82 wt % dopamine).

Workup

  1. customthe precipitated polymer was further purified
  2. customby dialyzing
  3. custom3500 MWCO dialysis tubing in deionized water for 24 hrs

Sources & evidence

ORD record
ord-f9c157cb43d24f5e80a679690e6d1877
Source dataset
uspto-grants-2011_10
Patent number
US08030413B2

Reaction notes

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