Reaktion #657287

Reaktionsgleichung

1-methoxy-4-methylamino-piperidine-4-carboxylic acid

methanol

thionyl chloride

→

1-methoxy-4-methylamino-piperidine-4-carboxylic acid methyl ester

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction mixture was heated
2. 2
   Temperaturat reflux overnight
3. 3
   TemperaturAfter cooling
4. 4
   Einengenthe mixture was concentrated
5. 5
   workup.ADDITIONthe residue diluted with ice water (20 ml)
6. 6
   ExtraktionThe aqueous phase was extracted with ethyl acetate (4×25 ml) and dichloromethane (4×50 ml)
7. 7
   Waschenthe combined organic layers washed with aqueous sodium bicarbonate (15 ml) and brine (15 ml)
8. 8
   Trocknendried over sodium sulfate
9. 9
   Einengenconcentrated
10. 10
    Sonstigethose described above under preparation example 6, step 2

Vorschrift

To a suspension of 1-methoxy-4-methylamino-piperidine-4-carboxylic acid (2.0 g, 10.63 mmol) in methanol (50 ml) at 0-10° C. was added thionyl chloride (2.29 ml, 3.76 g, 31.57 mmol) and the reaction mixture was heated at reflux overnight. After cooling, the mixture was concentrated, the residue diluted with ice water (20 ml) and neutralised with aqueous sodium bicarbonate. The aqueous phase was extracted with ethyl acetate (4×25 ml) and dichloromethane (4×50 ml), the combined organic layers washed with aqueous sodium bicarbonate (15 ml) and brine (15 ml), dried over sodium sulfate and concentrated. Yield: 0.76 g of 1-methoxy-4-methylamino-piperidine-4-carboxylic acid methyl ester (compound P5.4) as a viscous, orange oil. The spectral data of this crude material were identical to those described above under preparation example 6, step 2.

Quelle