Reaktion #215774

Reaktionsgleichung

triethylamine

2-Methoxy-4-(1-Boc-4-piperidyloxy)phenylacetic acid

4-(2-methylphenyl)piperazine-2-carboxamide

EDC

→

1-(2-methoxy-4-(1-Boc-4-piperdyloxy)phenylacetyl)-4-(2-methylphenyl)piperazine-2-carboxamide

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe mixture was concentrated in vacuo
2. 2
   Sonstigethe residue was partitioned between ethyl acetate and aqueous sodium bicarbonate
3. 3
   WaschenThe ethyl acetate layer was washed with
4. 4
   Trocknensodium bicarbonate and with brine, dried over sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Sonstigeevaporated to dryness in vacuo
7. 7
   SonstigeThe residue was chromatographed on silica gel
8. 8
   Wascheneluted with 3% methanol in methylene chloride
9. 9
   SonstigeThe combined product fractions were evaporated to dryness in vacuo

Vorschrift

2-Methoxy-4-(1-Boc-4-piperidyloxy)phenylacetic acid (331 mg, 0.91 mmol), 4-(2-methylphenyl)piperazine-2-carboxamide (200 mg, 0.91 mmol), EDC (209 mg, 1.09 mmol), and HBT (141 mg, 1.04 mmol) were combined in DMF (7 ml) under nitrogen. The mixture was adjusted to pH ca. 9 (moistened E. Merck colorpHast indicator) by addition of triethylamine (0.4 ml) and stirred at ambient temperature for 72 hours. The mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate and aqueous sodium bicarbonate. The ethyl acetate layer was washed with. sodium bicarbonate and with brine, dried over sodium sulfate, filtered, and evaporated to dryness in vacuo. The residue was chromatographed on silica gel eluted with 3% methanol in methylene chloride. The combined product fractions were evaporated to dryness in vacuo to give 1-(2-methoxy-4-(1-Boc-4-piperdyloxy)phenylacetyl)-4-(2-methylphenyl)piperazine-2-carboxamide.

Quelle