StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Ammonium Chloride → 1'-(benzyl)-spiro[isobenzofuran-1(3H),4'-piperidin]-3-thione

HRID 587645
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 587645
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][C:11]3([C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:15](=O)[O:14]3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:32]2)=CC=1.[NH4+].[Cl-]>C1(C)C=CC=CC=1>[CH2:7]([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[S:32])[O:14]2)[CH2:10][CH2:9]1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 87949Lawesson's reagentHCID 102664061'-Benzyl-3H-spiro[isobenzofuran-1,4'-piperidin]-3-one

Produkt 1

HCID 866679881'-(benzyl)-spiro[isobenzofuran-1(3H),4'-piperidin]-3-thione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To a mixture of 1′-(phenylmethyl)-spiro[isobenzofuran-1(3H),4′-piperidin]-3-one (25 g, 85.2 mmol) [C.A.S. 37663-42-6] in toluene (600 ml), was added 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide (Lawesson's reagent) (34.47 g, 85.2 mmol was added. The reaction mixture was heated at 140° C. for 2 h. After cooling, the mixture was poured into NH4Cl (aqueous sat. solution) and extracted with DCM. The organic phase was separated, dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography (silica gel; DCM/MeOH 3% as eluent). The desired fractions were collected and concentrated in vacuo to a residue that was purified by HPLC to yield intermediate D72 (8 g, 30.3%).

Aufarbeitung

  1. additionwas added
  2. temperatureAfter cooling
  3. extractionextracted with DCM
  4. customThe organic phase was separated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (silica gel; DCM/MeOH 3% as eluent)
  8. customThe desired fractions were collected
  9. concentrationconcentrated in vacuo to a residue that
  10. customwas purified by HPLC
  11. customto yield intermediate D72 (8 g, 30.3%)

Quellen und Nachweise

ORD-Eintrag
ord-10381f41c8724e6e96622a5b93b27e10
Quelldatensatz
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09226930B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion