Triethylamine → 2,6-dihydroxy-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-benzamide

HRID 929332

反応式

HRID 929332 の反応式
[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:24]=[CH:23][CH:22]=[C:21]([OH:25])[C:17]=1[C:18](O)=[O:19].C(N(CC)CC)C.O.ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C>CN(C)C=O>[OH:15][C:16]1[CH:24]=[CH:23][CH:22]=[C:21]([OH:25])[C:17]=1[C:18]([NH:13][CH2:12][CH2:11][C:8]1[C:4]2[C:3](=[CH:2][CH:1]=[C:6]([OH:7])[CH:5]=2)[NH:10][CH:9]=1)=[O:19]

参加物

7

反応物 5

HCID 8471TriethylamineHCID 93382,6-Dihydroxybenzoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 160436Serotonin HydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

生成物 1

HCID 666965052,6-dihydroxy-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-benzamide収率 14.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

Serotonin hydrochloride (430 mg, 2 mmol) and 2,6-dihydroxybenzoic acid (312 mg, 2 mmol) were dissolved in N,N-dimethylformamide (25 ml), and the solution temperature was maintained at 0° C. To this solution were added triethylamine (310 μl, 2.1 mmol), 1-hydroxybenzotriazole hydrate (HOBt H2O, 346 mg, 2.1 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI HCl, 429 mg, 2.1 mmol), the solution temperature was gradually warmed from 0° C. to room temperature, and the mixture was stirred at room temperature for 16 hours. The solvent was removed under reduced pressure, water (20 ml) was added to the residue, and the mixture was extracted twice with ethyl acetate (20 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, purified by preparative thin-layer chromatography (PTLC, eluent: ethyl acetate:hexane=3:1) to give 2,6-dihydroxy-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-benzamide (93 mg, yield 14.9%) as a powder.

後処理

  1. temperaturethe solution temperature was gradually warmed from 0° C. to room temperature
  2. customThe solvent was removed under reduced pressure, water (20 ml)
  3. additionwas added to the residue
  4. extractionthe mixture was extracted twice with ethyl acetate (20 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:hexane=3:1)

出典と根拠

ORDレコード
ord-ed6711017c25491fa26933f9ccd8f801
出典データセット
uspto-grants-2016_03
特許番号
US09295624B2

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