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

HRID 628779노트

반응식

HRID 628779 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e9ffdf15c91c4643baa1f7dcbafe5300
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315459B2

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