Triethylamine → 4-(3-Indolyl)-1-[(4-oxo-3-thiazolidinyl)acetyl]piperidine

HRID 34910

Reaktionsgleichung

Reaktionsgleichung von HRID 34910
[O:1]=[C:2]1[CH2:6][S:5][CH2:4][N:3]1[CH2:7][C:8](Cl)=[O:9].[NH:11]1[CH2:16][CH2:15][CH:14]([C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19][CH:18]=2)[CH2:13][CH2:12]1.C(N(CC)CC)C>O1CCCC1.C(Cl)(Cl)Cl>[NH:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:17]([CH:14]2[CH2:15][CH2:16][N:11]([C:8](=[O:9])[CH2:7][N:3]3[C:2](=[O:1])[CH2:6][S:5][CH2:4]3)[CH2:12][CH2:13]2)=[CH:18]1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 7022353-(4-Piperidinyl)-1H-indoleHCID 212972254-Oxo-3-thiazolidinylacetyl chloride

Produkt 1

HCID 212972224-(3-Indolyl)-1-[(4-oxo-3-thiazolidinyl)acetyl]piperidineAusbeute 27,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 4-oxo-3-thiazolidinylacetyl chloride (1.75 g) in tetrahydrofuran (5.00 ml) was added dropsise to a suspension of 3-(4-piperidyl)indole (2.00 g) and triethylamine (4.10 ml) in a mixture of tetrahydrofuran (15.0 ml) and chloroform (5.00 ml) at 4° to 7° C. with stirring. After the mixture was allowed to stir for 1 hour with ice-bath cooling, the resultant precipitate was removed by filtration and the solvent was evaporated in vacuo. The residue was mixed with saturated aqueous sodium hydrogen carbonate (10.0 ml) and the mixture was extracted with chloroform (20.0 ml). The extract was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was recrystallized from a mixture of methanol and acetone to give 4-(3-indolyl)-1-[(4-oxo-3-thiazolidinyl)acetyl]piperidine (0.92 g) as slightly brown prisms.

Aufarbeitung

  1. stirringto stir for 1 hour with ice-bath
  2. temperaturecooling
  3. customthe resultant precipitate was removed by filtration
  4. customthe solvent was evaporated in vacuo
  5. additionThe residue was mixed with saturated aqueous sodium hydrogen carbonate (10.0 ml)
  6. extractionthe mixture was extracted with chloroform (20.0 ml)
  7. washThe extract was washed with water
  8. dry with materialdried over magnesium sulfate
  9. customevaporated in vacuo
  10. customThe residue was recrystallized from a mixture of methanol and acetone

Quellen und Nachweise

ORD-Eintrag
ord-0003897d204849bf86b2e0ba626abee7
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04764514

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