Triethylamine → 1-Methanesulfonyl-N-(5-phenyl-2-pyrazinyl)spiro[indoline-3,4'-piperidine]-1'-carboxamide

HRID 989049Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 989049
[C:1]1([C:7]2[N:8]=[CH:9][C:10]([NH:13][C:14](=[O:22])OC3C=CC=CC=3)=[N:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH3:24][S:25]([N:28]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:30]2([CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[CH2:29]1)(=[O:27])=[O:26].CCN(CC)CC>C(Cl)(Cl)Cl.CCOC(C)=O>[CH3:24][S:25]([N:28]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:30]2([CH2:31][CH2:32][N:33]([C:14]([NH:13][C:10]3[CH:9]=[N:8][C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[CH:12][N:11]=3)=[O:22])[CH2:34][CH2:35]2)[CH2:29]1)(=[O:26])=[O:27]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 9879110Phenyl 5-phenylpyrazin-2-ylcarbamateHCID 219560841-(Methylsulfonyl)spiro[indoline-3,4'-piperidine] hydrochloride

Produkt 1

HCID 121087811-Methanesulfonyl-N-(5-phenyl-2-pyrazinyl)spiro[indoline-3,4'-piperidine]-1'-carboxamideAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of phenyl N-(5-phenyl-2-pyrazinyl)carbamate 1-2 (7, 350 mg, 1.20 mmol), 1-methylsulfonylspiro[indoline-3,4′-piperidine]hydrochloride 1-3 (400 mg, 1.32 mmol) and Et3N (0.5 mL, 3.6 mmol) in CHCl3 (6 mL) was heated to reflux for 3 h. After cooling, the mixture was diluted with EtOAc, washed with 10% citric acid, sat. NaHCO3 and brine, dried over MgSO4, and concentrated under reduced pressure to start precipitation. The precipitate was collected by filtration and dried in vacuio to give 100 (517 mg, 93%) as a white powder.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 3 h
  3. temperatureAfter cooling
  4. washwashed with 10% citric acid, sat. NaHCO3 and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customprecipitation
  8. filtrationThe precipitate was collected by filtration
  9. customdried in vacuio

Quellen und Nachweise

ORD-Eintrag
ord-61921fd259ca418c9badf948f7935afd
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06638942B1

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