تفاعل #1726678

معادلة التفاعل

hydrochloric acid

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

NaOH

→

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

المذيبات

acetic acid

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةunder reflux overnight
2. 2
   استخلاصthe unclear solution was extracted with ethyl acetate (2×40 ml)
3. 3
   تجفيفThe combined organic phases were dried (MgSO4)
4. 4
   أخرىthe 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
   أخرىThe target compound was collected as a white oxalic salt
8. 8
   أخرىRT=2.24

الإجراء التجريبي

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%).

المصدر