Reaktion #336235

Reaktionsgleichung

methyl 4-fluorobenzoate

4-(2-hydroxyethyl)piperdine

water

→

crude product

Ausbeute 71.0%

1-(4'-Methoxycarbonylphenyl)-4-(2-hydroxyethyl)piperdine

Ausbeute 71.0%

Lösungsmittel

N-methylpyrrolidin-2-one

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe dark solution was cooled
2. 2
   FiltrationThe tan precipitate was filtered off
3. 3
   Waschenwashed well with water

Vorschrift

A solution of 9.84 grams of methyl 4-fluorobenzoate (63.9 mmol) and 12.40 grams of 4-(2-hydroxyethyl)piperdine (96 mmol) in 50 mL N-methylpyrrolidin-2-one was heated to 110°-120° C. and stirred for 72 hours. The dark solution was cooled and poured into 400 mL water. The tan precipitate was filtered off and washed well with water to yield 11.89 grams of crude product as a tan powder (71%). The crude material was recrystallized once from 100 mL ethanol which gave 4.75 grams (40% recovery) of a tan powder. Melting point 110°-115° C. 2H NMR δ (acetone-d6): 1.27 (2H, quad of doub, J=3.8 hz & 12.2 hz); 1.47 (2H, quad, J=6.6 hz); 1.71 (1H, mult); 1.80 (2H, br doub); 2.83 (2H, trip of doub, J=2.5 hz & 12.6 hz); 3.62 (2H, trip, J=6.6 hz); 3.78 (3H, s); 3.92 (2H, br doub); 6.93 (2H, doub); 7.81 (2H, doub). 13C NMR δ (acetone-d6): 32.59, 33.36, 40.30, 48.61, 51.55, 59.81, 114.30, 119.26, 132.0, 155.29, 167.18.

Quelle