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

HRID 722116노트

반응식

HRID 722116 반응식
Cl.C(OC([N:9]1[CH2:14][CH2:13][C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[S:22][C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)(O)[CH2:11][CH2:10]1)=O)(C)(C)C.[OH-].[Na+]>C(O)(=O)C>[CH3:29][C:26]1[CH:27]=[CH:28][C:23]([S:22][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[C:12]2[CH2:13][CH2:14][NH:9][CH2:10][CH:11]=2)=[CH:24][CH:25]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 218649151-Tert-butoxycarbonyl-4-[2-(4-methylphenylsulfanyl)phenyl]piperidin-4-ol

생성물 1

HCID 98143014-[2-(4-Methylphenylsulfanyl)phenyl]-3,6-dihydro-2H-pyridine

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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%).

후처리

  1. temperatureunder reflux overnight
  2. extractionthe unclear solution was extracted with ethyl acetate (2×40 ml)
  3. dry with materialThe combined organic phases were dried (MgSO4)
  4. customthe solvents evaporated in vacuo
  5. dissolutionThe crude material (0.48 g) was dissolved in ethyl acetate (3.2 mL) at 50° C.
  6. additiona solution of oxalic acid (0.11 g) in EtOH (3.2 mL) was slowly added
  7. customThe target compound was collected as a white oxalic salt
  8. customRT=2.24

출처 및 근거

ORD 기록
ord-69d120da63ed4b4f8e8a16ccb440fd8f
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07138407B2

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