Acetic Acid → cis-2-(4-Pyridylethyl)-3a,4,7,7a-tetrahydroisoindoline

HRID 1586772Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1586772
[CH2:1]1[C@@H:9]2[C@@H:4]([CH2:5][CH:6]=[CH:7][CH2:8]2)[CH2:3][NH:2]1.[CH:10]([C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1)=[CH2:11].C(O)(=O)C>CO>[N:15]1[CH:16]=[CH:17][C:12]([CH2:10][CH2:11][N:2]2[CH2:3][C@H:4]3[C@H:9]([CH2:8][CH:7]=[CH:6][CH2:5]3)[CH2:1]2)=[CH:13][CH:14]=1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 75024-VinylpyridineHCID 16765331cis-2,3,3a,4,7,7a-Hexahydro-1h-isoindole

Produkt 1

HCID 70072088cis-2-(4-Pyridylethyl)-3a,4,7,7a-tetrahydroisoindoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 0.64 g of cis-3a,4,7,7a-tetrahydroisoindoline, 0.6 mL of 4-vinylpyridine, 0.4 mL of acetic acid and 10 mL of methanol was heated under reflux for 16 hours. Removal of the solvent and short-path distillation of the residue (160° bath temperature, 0.002 mm) gave 0.74 g. of cis-2-(4-pyridylethyl)-3a,4,7,7a-tetrahydropyridine. 1H NMR (in CDCl3) δ8.5 (d, 2H); 7.1 (d, 2H); 5.8 (m, 2H); 3.0 (m, 2H); 2.7-2.8(m, 4H); 2.4 (m, 2H); 2.2-2.3 (m, 4H) and 1.9 (d, 2H). The dihydrochloride hemi-hydrate had an indefinite melting point after crystallization from 2-propanol.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. customRemoval of the solvent and short-path distillation of the residue (160° bath temperature, 0.002 mm)
  4. customgave 0.74 g
  5. customafter crystallization from 2-propanol

Quellen und Nachweise

ORD-Eintrag
ord-e5c5f66ee4c04d248bd4df365db4c5e3
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05216018

Notizen zur Reaktion

Wird geladen…