Trifluoroacetic acid → 4-[(4-Bromophenyl)thio]piperidine

HRID 2288725노트

반응식

HRID 2288725 반응식
FC(F)(F)C(O)=O.[Br:8][C:9]1[CH:28]=[CH:27][C:12]([S:13][CH:14]2[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]2)=[CH:11][CH:10]=1>ClCCl>[Br:8][C:9]1[CH:28]=[CH:27][C:12]([S:13][CH:14]2[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]2)=[CH:11][CH:10]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 11760469tert-Butyl 4-((4-bromophenyl)thio)piperidine-1-carboxylate

생성물 1

HCID 234994844-[(4-Bromophenyl)thio]piperidine수율 100%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
5 °C

실험 절차

Trifluoroacetic acid (7.5 ml) was added in portions to a stirred, ice-cooled solution of 4-(4-bromothiophenoxy)-1-t-butoxycarbonylpiperidine (2.6 g) in dry dichloromethane (5 ml) under an atmosphere of argon so that the temperature of the mixture was maintained between 5 and 10° C. The solution was stirred at 5° C. for 1 hour, then at ambient temperature for 2 hours. The solution was evaporated. The residual oil was treated with a saturated aqueous solution of sodium carbonate and extracted with ethyl acetate (3×70 ml). The ethyl acetate extracts were combined, dried (Na2SO4) and evaporated. The residue was purified by flash column chromatography on silica gel, using a mixture of 95:5:3, ethyl acetate:methanol:aqueous ammonia (density 0.88 g/cm3) as eluent, to give 4-(4-bromothiophenoxy)piperidine (1.9 g) as an off-white solid;

후처리

  1. temperaturewas maintained between 5 and 10° C
  2. waitat ambient temperature for 2 hours
  3. customThe solution was evaporated
  4. additionThe residual oil was treated with a saturated aqueous solution of sodium carbonate
  5. extractionextracted with ethyl acetate (3×70 ml)
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customThe residue was purified by flash column chromatography on silica gel
  9. additiona mixture of 95:5:3, ethyl acetate

출처 및 근거

ORD 기록
ord-74a2b22ee88343418ee1f9f20023ed91
출처 데이터셋
uspto-grants-2000_07
특허 번호
US06090813

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