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Ammonia → 5-(Cyclooctyl-methyl)-spiro[indoline-3,4'-piperidin]-2-one

HRID 1441674
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1441674
N.[Li].C([N:10]1[C:23]2[C:18](=[CH:19][C:20]([CH2:24][CH:25]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)=[CH:21][CH:22]=2)[C:12]2([CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[C:11]1=[O:33])C1C=CC=CC=1.[Cl-].[NH4+]>C1COCC1>[CH:25]1([CH2:24][C:20]2[CH:19]=[C:18]3[C:12]4([CH2:13][CH2:14][NH:15][CH2:16][CH2:17]4)[C:11](=[O:33])[NH:10][C:23]3=[CH:22][CH:21]=2)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 3028194LithiumHCID 685388831-Benzyl-5-(cyclooctyl-methyl)-spiro[indoline-3,4'-piperidin]-2-one

Produkt 1

HCID 685404665-(Cyclooctyl-methyl)-spiro[indoline-3,4'-piperidin]-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a magnetically stirred solution of liquid ammonia (10 mL) was added lithium (20 mg) at −78° C. under nitrogen atmosphere causing the solution to turn dark-blue. To the reaction mixture was then added a solution of 1-benzyl-5-(cyclooctyl-methyl)-spiro[indoline-3,4′-piperidin]-2-one (0.025 g, 0.06 mmol) in dry THF (2 mL). The reaction mixture was stirred −78° C. under nitrogen atmosphere for a few minutes, then ammonium chloride was added and the reaction mixture was stirred at room temperature for one hour. The reaction mixture was partitioned with water and ethyl acetate. The organic layer was washed with brine, dried with Na2SO4, filtered and the solvent evaporated in vacuo to yield the title compound as a foam.

Aufarbeitung

  1. stirringthe reaction mixture was stirred at room temperature for one hour
  2. customThe reaction mixture was partitioned with water and ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. customthe solvent evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-741b9802c2fa4a0ead88a081a94898b6
Quelldatensatz
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07655670B2

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