Triethylamine → HCID 66696499, compound

HRID 929327Notes

Reaction equation

HRID 929327 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][C:4]2[C:8]([CH2:11][CH2:12][NH2:13])=[CH:9][NH:10][C:3]=2[CH:2]=1.Cl.[OH:15][C:16]1[CH:26]=[C:25]([OH:27])[CH:24]=[CH:23][C:17]=1/[CH:18]=[CH:19]/[C:20](O)=[O:21].C(N(CC)CC)C.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>ClCCl.CN(C)C=O>[OH:7][C:6]1[CH:5]=[C:4]2[C:3](=[CH:2][CH:1]=1)[NH:10][CH:9]=[C:8]2[CH2:11][CH2:12][NH:13][C:20](=[O:21])[CH:19]=[CH:18][C:17]1[CH:23]=[CH:24][C:25]([OH:27])=[CH:26][C:16]=1[OH:15]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 160436Serotonin HydrochlorideHCID 446611614-86-8HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 66696499HCID 66696499, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Serotonin hydrochloride (300 mg, 1.41 mmol) and trans-2,4-dihydroxycinnamic acid (253 mg, 1.41 mmol) were dissolved in a mixed solvent of dichloromethane (6 ml) and N,N-dimethylformamide (6 ml), and the solution was maintained at 0° C. To this solution were added triethylamine (216 μl, 1.55 mmol), 1-hydroxybenzotriazole hydrate (HOBt H2O, 237 mg, 1.55 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI HCl, 297 mg, 1.55 mmol), and the mixture was gradually warmed to room temperature and stirred at room temperature for 16 hours. The solvent was removed under reduced pressure, water (10 ml) was added to the residue, and the mixture was extracted twice with ethyl acetate (10 ml). The ethyl acetate layer was washed twice with 5% aqueous citric acid solution (5 ml), once with saturated brine (5 ml), twice with 5% aqueous sodium hydrogen carbonate solution (5 ml), and once with saturated brine (5 ml), and dried over anhydrous magnesium sulfate. Magnesium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure, and purified by preparative thin-layer chromatography (PTLC, eluent: ethyl acetate-n-hexane=2:1, 0.01% formic acid) to give N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(2,4-dihydroxyphenyl)-2-propenamide (243 mg, yield 51.0%) as a viscous oil.

Workup

  1. temperaturethe mixture was gradually warmed to room temperature
  2. customThe solvent was removed under reduced pressure, water (10 ml)
  3. additionwas added to the residue
  4. extractionthe mixture was extracted twice with ethyl acetate (10 ml)
  5. washThe ethyl acetate layer was washed twice with 5% aqueous citric acid solution (5 ml), once with saturated brine (5 ml), twice with 5% aqueous sodium hydrogen carbonate solution (5 ml)
  6. dry with materialonce with saturated brine (5 ml), and dried over anhydrous magnesium sulfate
  7. customMagnesium sulfate was removed by filtration
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. custompurified by preparative thin-layer chromatography (PTLC, eluent: ethyl acetate-n-hexane=2:1, 0.01% formic acid)

Sources & evidence

ORD record
ord-9dc49180f42a4750bb3e7c166c361bfd
Source dataset
uspto-grants-2016_03
Patent number
US09295624B2

Reaction notes

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