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

HRID 1528002Notes

Reaction equation

HRID 1528002 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-5e983f4f2d1945688729589883a8dc90
Source dataset
uspto-grants-2015_07
Patent number
US09090575B2

Reaction notes

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