Toluene → Ethyl 4-(2-(4-tolylsulfanyl)phenyl)-piperidin-1-carboxylate

HRID 628779Notes

Reaction equation

HRID 628779 reaction equation
FC(F)(F)C(O)=O.C([SiH](CC)CC)C.O[C:16]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[S:33][C:34]2[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=2)[CH2:21][CH2:20][N:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:18][CH2:17]1.C1(C)C=CC=CC=1>O>[C:37]1([CH3:40])[CH:38]=[CH:39][C:34]([S:33][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[CH:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:18][CH2:17]2)=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 452583081-Carbethoxy-4-hydroxy-4-[2-(4-methylphenylsulfanyl)phenyl]piperidine

Product 1

HCID 45258309Ethyl 4-(2-(4-tolylsulfanyl)phenyl)-piperidin-1-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Trifluoroacetic acid (2.8 kg, 24.9 mol) and triethylsilane (362 g, 3.1 mol) was charged in a reactor with an efficient stirrer. Ethyl 4-hydroxy-4-(2-(4-tolylsulfanyl)phenyl)-piperidin-1-carboxylate (462 g, 1.24 mol) was added via a powder funnel in portions. The reaction was slightly exothermic. The temperature rose to 50° C. After the addition was finalised the reaction mixture was warmed to 60° C. for 18 hours. The reaction mixture was cooled down to room temperature. Toluene (750 mL) and water (750 mL) was added. The organic phase was isolated and the aqueous phase was extracted with another portion of toluene (750 mL). The organic phases were combined and washed with sodium chloride solution (15%, 500 mL) and dried over sodium sulphate. The sodium sulphate was filtered off, the filtrate evaporated at reduced pressure to a red oil which was processed further in the next step.

Workup

  1. customrose to 50° C
  2. additionAfter the addition
  3. temperatureThe reaction mixture was cooled down to room temperature
  4. customThe organic phase was isolated
  5. extractionthe aqueous phase was extracted with another portion of toluene (750 mL)
  6. washwashed with sodium chloride solution (15%, 500 mL)
  7. dry with materialdried over sodium sulphate
  8. filtrationThe sodium sulphate was filtered off
  9. customthe filtrate evaporated at reduced pressure to a red oil which

Sources & evidence

ORD record
ord-e9ffdf15c91c4643baa1f7dcbafe5300
Source dataset
uspto-grants-2016_04
Patent number
US09315459B2

Reaction notes

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