Ammonia → 4-(Piperidin-3-yl)-1H-indole

HRID 1155683Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1155683
[Li].N.Cl.[NH:4]1[C:12]2[C:7](=[C:8]([C:13]3(O)[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]3)[CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5]1.O1CCCC1>C(O)C>[NH:15]1[CH2:16][CH2:17][CH2:18][CH:13]([C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[C:7]=2[CH:6]=[CH:5][NH:4]3)[CH2:14]1

Komponenten

6

Edukt 4

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 3028194LithiumHCID 12900686HCID 12900686, Verbindung

Produkt 1

HCID 30677184-(Piperidin-3-yl)-1H-indoleAusbeute 69,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

700 mg of lithium were added in small fractions over one hour at -40° C. to a mixture of 100 ml of ammonia, 1.2 g of 3-(1H-indol-4-yl)-3-piperidinol hydrochloride, 20 ml of tetrahydrofuran and 10 ml of anhydrous ethanol and the ammonia was evaporated at room temperature. The residue was taken up in 100 ml of water and the aqueous phase was extracted with chloroform containing 10% methanol. The organic phase was washed with water, dried and filtered. The filtrate was evaporated to dryness and the 950 mg of residue was chromatographed over silica gel. Elution with a 7-2-1-chloroform-methanol-triethylamine mixture yielded 665 mg of 4-(piperidin-3-yl)-1H-indole.

Aufarbeitung

  1. customthe ammonia was evaporated at room temperature
  2. extractionthe aqueous phase was extracted with chloroform containing 10% methanol
  3. washThe organic phase was washed with water
  4. customdried
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customthe 950 mg of residue was chromatographed over silica gel
  8. washElution with a 7-2-1-chloroform-methanol-triethylamine mixture

Quellen und Nachweise

ORD-Eintrag
ord-878a87cde2ab4eaa863a2bca5ecc1717
Quelldatensatz
uspto-grants-1982_06
Patentnummer
US04332808

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