Réaction #1726678

Équation de réaction

hydrochloric acid

1-tert-butoxycarbonyl-4-[2-(4-methylphenylsulfanyl)phenyl]piperidin-4-ol

NaOH

→

4-[2-(4-Methylphenylsulfanyl)phenyl]-3,6-dihydro-2H-pyridine

Solvants

acetic acid

Conditions de réaction

Traitement

1. 1
   Températureunder reflux overnight
2. 2
   Extractionthe unclear solution was extracted with ethyl acetate (2×40 ml)
3. 3
   SéchageThe combined organic phases were dried (MgSO4)
4. 4
   Autrethe solvents evaporated in vacuo
5. 5
   workup.DISSOLUTIONThe crude material (0.48 g) was dissolved in ethyl acetate (3.2 mL) at 50° C.
6. 6
   workup.ADDITIONa solution of oxalic acid (0.11 g) in EtOH (3.2 mL) was slowly added
7. 7
   AutreThe target compound was collected as a white oxalic salt
8. 8
   AutreRT=2.24

Mode opératoire

Concentrated aq hydrochloric acid (10 ml) was added to a stirred solution of 1-tert-butoxycarbonyl-4-[2-(4-methylphenylsulfanyl)phenyl]piperidin-4-ol (0.84 g, 2.1 mmol) in acetic acid (30 mL). The solution was boiled under reflux overnight, cooled to room temperature and then stirred in an ice bath. An aqueous solution of NaOH (9.1 M, 40 mL) was slowly added and the unclear solution was extracted with ethyl acetate (2×40 ml). The combined organic phases were dried (MgSO4) and the solvents evaporated in vacuo. The crude material (0.48 g) was dissolved in ethyl acetate (3.2 mL) at 50° C. and a solution of oxalic acid (0.11 g) in EtOH (3.2 mL) was slowly added. The target compound was collected as a white oxalic salt. 1H (DMSO-d6) δ 7.3-7.2 (m, 7H); 7.15 (m, 1H); 7.00 (m, 1H); 5.6 (d, 1H); 3.7 (d, 2H); 3.25 (t, 2H); 2.6 (m, 2H); 2.3 (s, 3H). LC/MS (m/z) 282.2 (MH+); RT=2.24; purity (UV, ELSD): 99%, 100%; yield: 0.31 g (40%).

Source