Phenol → 4-(2-Chlorophenylsulfanyl)piperidine hydrochloride

HRID 236101

반응식

HRID 236101 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH:9]1[CH2:14][CH2:13][N:12](S(C2C=CC(C)=CC=2)(=O)=O)[CH2:11][CH2:10]1.C1(O)C=CC=CC=1.[OH-].[Na+]>Br>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1

참가 물질

5

반응물 3

HCID 996PhenolHCID 14798Sodium HydroxideHCID 136079634-[(2-Chlorophenyl)thio]-1-[(4-methylphenyl)sulfonyl]piperidine

생성물 1

HCID 177498024-(2-Chlorophenylsulfanyl)piperidine hydrochloride

시약·촉매·용매 1

HCID 260Hydrogen Bromide용매

실험 절차

A mixture of 88.76 g (0.23 mole) of 4-[(2-chlorophenyl)thio]-1-[(4-methylphenyl)sulfonyl]piperidine, 47.0 g (0.50 mole) of phenol and 200 ml of 48% hydrobromic acid was refluxed for 1.5 hr. The reaction mixture was cooled to room temperature and diluted with ice water. The mixture was made alkaline with 50% sodium hydroxide and extracted with diethyl ether. The ether phase was extracted with 1N sulfuric acid. The acidic layer was made alkaline and extracted with methylene chloride. The methylene chloride layer was dried over sodium sulfate, filtered and evaporated to give an oil, the free base of the title compound. The free base was converted to 4.30 g (36.5%) of a white crystalline hydrochloride salt, m.p. 202°-210° C.

후처리

  1. temperaturewas refluxed for 1.5 hr
  2. extractionextracted with diethyl ether
  3. extractionThe ether phase was extracted with 1N sulfuric acid
  4. extractionextracted with methylene chloride
  5. dry with materialThe methylene chloride layer was dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto give an oil

출처 및 근거

ORD 기록
ord-2fd37515aeae47f5b6dce823bd9360b4
출처 데이터셋
uspto-grants-1987_02
특허 번호
US04642348

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