Reaktion #93163

Reaktionsgleichung

1-(2-aminobenzoyl)piperidine

4-chloropyridine hydrochloride

→

1-[2-(4-pyridinylamino)benzoyl]piperidine

Ausbeute 65.8%

Lösungsmittel

2-methoxyethanol

2-methoxyethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstige(125° C. internal temperature)
2. 2
   Sonstigewas collected
3. 3
   TemperaturHeating
4. 4
   workup.WAITwas continued for another hour while 16 liters of distillate
5. 5
   Sonstigewas collected
6. 6
   EinengenThe reaction mixture was concentrated in vacuo
7. 7
   workup.DISSOLUTIONthe thick residue was dissolved in 10 liters of water
8. 8
   workup.ADDITIONSodium acetate trihydrate (1.85 kg) was added
9. 9
   Waschenthe solution washed three times with 3 liters of isopropyl acetate
10. 10
    workup.ADDITIONby dropwise addition of sodium hydroxide solution
11. 11
    workup.ADDITIONSeeding during the addition
12. 12
    workup.ADDITIONA small amount of acetic acid was added
13. 13
    Sonstigewas collected
14. 14
    Waschenwashed with water and air
15. 15
    Sonstigedried

Vorschrift

A solution of 2.77 kg 1-(2-aminobenzoyl)piperidine in 16 liters of 2-methoxyethanol was heated until solvent distillation was about to begin (125° C. internal temperature). A solution of 2.1 kg 4-chloropyridine hydrochloride in 21 liters of 2-methoxyethanol was then slowly added over a period of one hour during which 4 liters of distillate was collected. Heating was continued for another hour while 16 liters of distillate was collected. The reaction mixture was concentrated in vacuo, and the thick residue was dissolved in 10 liters of water. Sodium acetate trihydrate (1.85 kg) was added and the solution washed three times with 3 liters of isopropyl acetate and decolorized with activated charcoal. The aqueous solution was made basic (pH>10) by dropwise addition of sodium hydroxide solution. Seeding during the addition generated a precipitate. A small amount of acetic acid was added to lower the pH to 8.5-9, and after 30 minutes of stirring the product was collected, washed with water and air dried to give 2.51 kg of 1-[2-(4-pyridinylamino)benzoyl]piperidine, m.p. 152°-153° C. The latter product was further purified by recrystallization from acetone to give the compound with m.p. 154°-155° C.

Quelle