Reaktion #347368

Reaktionsgleichung

3-{N-[β-(3,4-diacetoxyphenyl)ethyl]}carbamoylpyridine

compound 8c

3-{N-[β-(3,4-Dipivalyloxyphenyl)ethyl]}carbamoylpyridine

methyl iodide

→

1-Methyl-3-{N-[β-(3,4-diacetoxyphenyl)ethyl]}carbamoylpyridinium iodide

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was refluxed overnight
2. 2
   SonstigeThe acetone solution was then decanted from the insoluble oily residue
3. 3
   workup.ADDITIONEther was added to the acetone solution
4. 4
   Sonstigethe solid which separated
5. 5
   Sonstigewas crystallized from acetone/ether
6. 6
   SonstigeYield

Vorschrift

To a solution of 1.71 g (5 mmol) of 3-{N-[β-(3,4-diacetoxyphenyl)ethyl]}carbamoylpyridine (prepared like compound 8c), 1.41 g (10 mmol) of methyl iodide were added and the mixture was refluxed overnight under stirring. The acetone solution was then decanted from the insoluble oily residue. Ether was added to the acetone solution and the solid which separated was crystallized from acetone/ether. Yield, 1.9 g (78%) of yellow crystalline needles, m.p. 171°-173° C. U.V. (methanol) 215, 265 nm; NMR (D2O) δ 8.86-7.63 (ms, 4H, C5H4N+), 6.66 (bs, 3H, C6H3), 4.4 (s, 3H, --N+ --CH3), 3.50 (t, 2H, --N--CH2), 3.03 (t, 2H, CH2), 2.21 (bs, 6H, 2 COCH3). Anal. Calcd for C19H21IN2O5 : C, 47.12; H, 4.37; N, 5.78. Found: C, 47.23; H, 4.38; N, 5.78.

Quelle