Triethylamine → 1'-Benzylspiro[isochroman-1,4'-piperidine]

HRID 1182728노트

반응식

HRID 1182728 반응식
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:21][CH2:22]O)([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.CS(Cl)(=O)=O>>[CH2:1]([N:8]1[CH2:9][CH2:10][C:11]2([C:15]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:21][CH2:22][O:14]2)[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 673640824-[2-(Hydroxyethyl)phenyl]-1-benzylpiperidin-4-ol

생성물 1

HCID 102664131'-Benzylspiro[isochroman-1,4'-piperidine]수율 21%

실험 절차

To a solution of 1-benzyl-4-[2-(2-hydroxy-ethyl)-phenyl]-piperidin-4-ol (2.0 g, 6.6 mmol) and triethylamine (1.9 ml, 14 mmol) dry tetrahydrofuran (50 ml) was added methanesulfonyl chloride (0.48 ml, 6.2 mmol) at room temperature. The reaction mixture was heated at reflux for 4 h. Quenching with water and basification with 1 M aqueous sodium hydroxide solution was followed by extraction with three portions of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. Flash chromatography of the crude product with n-heptane/ethyl acetate as eluent gave the title compound (0.40 g, 21%) as yellow oil. MS m/e: 294 (M+H+).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 4 h
  3. customQuenching with water and basification with 1 M aqueous sodium hydroxide solution
  4. extractionwas followed by extraction with three portions of ethyl acetate
  5. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-8920f10f20f44dcf930392ae95ba2f28
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08664216B2

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