Sodium Iodide → 4-(4-Hydroxypiperidinyl)butyrophenone

HRID 324536

Reaktionsgleichung

Reaktionsgleichung von HRID 324536
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Cl[CH2:9][CH2:10][CH2:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13].[Na+].[I-].C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1>[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:9][CH2:10][CH2:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:13])[CH2:4][CH2:3]1

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 79341Piperidin-4-olHCID 2535334-Chlorobutyrophenone

Produkt 1

HCID 4252714-(4-Hydroxypiperidinyl)butyrophenoneAusbeute 3,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 4-hydroxypiperidine (550 mg, 5.4 mmol), 4-chlorobutyrophenone (490 mg, 2.7 mmol), NaI (160 mg), K2CO3 (760 mg) and toluene (25 mL) was refluxed for 24 h, cooled to rt, filtered and washed with hexane (2×10 mL). The filtrate was evaporated, and the residue was chromatographed over silica gel (EtOAc-EtOH-NH4OH, 60:40:2) to give 21 mg (3%) of the free base as a yellow powder, mp 101-2° C. 1H NMR (CDCl3-D2O): 1.50-1.57 (m, 2H), 1.83-1.98 (m, 3H), 2.08-2.17 (m, 3H), 2.397 (t, 2H, J=7), 2.73-2.78 (m, 2H), 3.00 (t, 2H, J=7), 3.60-3.70 (m, 1H), 7.43-7.56 (m, 3H), 7.96-7.98 (m, 2H). Analysis, Calcd for C15H21NO2: C, 72.84, H, 8.56, N, 5.66; Found: C, 72.31, H, 8.45, N, 5.32.

Aufarbeitung

  1. temperaturewas refluxed for 24 h
  2. filtrationfiltered
  3. washwashed with hexane (2×10 mL)
  4. customThe filtrate was evaporated
  5. customthe residue was chromatographed over silica gel (EtOAc-EtOH-NH4OH, 60:40:2)

Quellen und Nachweise

ORD-Eintrag
ord-78a5a37638f943e398f31324dc69c977
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06218404B1

Verknüpfte Notizen

Wird geladen…