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

HRID 2288725ノート

反応式

HRID 2288725 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
5 °C

実験手順

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;

後処理

  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

出典と根拠

ORDレコード
ord-74a2b22ee88343418ee1f9f20023ed91
出典データセット
uspto-grants-2000_07
特許番号
US06090813

反応ノート

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