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

HRID 1182728ノート

反応式

HRID 1182728 の反応式
[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

参加物

4

反応物 3

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

生成物 1

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

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-8920f10f20f44dcf930392ae95ba2f28
出典データセット
uspto-grants-2014_03
特許番号
US08664216B2

反応ノート

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