Triethylamine → Dopamine

HRID 1056473Notes

Reaction equation

HRID 1056473 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.ON1C(=O)CCC1=O.[CH:24]1[C:29]([CH2:30][CH2:31][NH2:32])=[CH:28][C:27]([OH:33])=[C:26]([OH:34])[CH:25]=1.Cl.CCN(CC)CC>CN(C=O)C>[NH2:32][CH2:31][CH2:30][C:29]1[CH:24]=[CH:25][C:26]([OH:34])=[C:27]([OH:33])[CH:28]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 65340Dopamine HydrochlorideHCID 80170N-Hydroxysuccinimide

Product 1

HCID 681Dopamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

MTC-OH (1.024 g, 6.4 mmol), dicyclohexylcarbodiimide (DCC, 1.319 g, 6.4 mmol) and N-hydroxysuccinimide (NHS, 0.736 g, 6.4 mmol) were charged in a 100 mL round bottom flask and dissolved in 8 mL of dry DMF before put in a ice bath. Dopamine.HCl (1.092 g, 5.76 mmol) and Et3N (1.685 mL, 12.1 mmol) was dissolved in 8 mL of dry DMF and added dropwise to the above solution under N2 atmosphere. The ice bath was removed after 3 hours and the reaction continued overnight. Then, the reaction solution was precipitated in DCM and a mixture of THF and Et2O (v/v=1:1) sequentially. Finally, the filtrate was concentrated, precipitated in Et2O and washed with Et2O for three times to give MTC-dopamine.

Workup

  1. additionadded dropwise to the above solution under N2 atmosphere
  2. customThe ice bath was removed after 3 hours
  3. customthe reaction continued overnight
  4. customThen, the reaction solution was precipitated in DCM
  5. additiona mixture of THF and Et2O (v/v=1:1) sequentially
  6. concentrationFinally, the filtrate was concentrated
  7. customprecipitated in Et2O
  8. washwashed with Et2O for three times

Sources & evidence

ORD record
ord-6bccb1d6bc87429caddda786807f2ba0
Source dataset
uspto-grants-2016_07
Patent number
US09399044B2

Reaction notes

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