Hydrochloric Acid → Spiro[isochroman-4,4'-piperidine]

HRID 1182731

反応式

HRID 1182731 の反応式
[C:1]1([C:7]2([CH2:13][OH:14])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C=O.O1CCOC[CH2:18]1.Cl>C(OCC)(=O)C>[NH:10]1[CH2:9][CH2:8][C:7]2([C:1]3[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:18][O:14][CH2:13]2)[CH2:12][CH2:11]1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 312751,4-DioxaneHCID 778964-Phenylpiperidine-4-methanol

生成物 1

HCID 10847614Spiro[isochroman-4,4'-piperidine]収率 50%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of (4-phenyl-piperidin-4-yl)-methanol (0.1 g, 0.5 mmol), paraformaldehyde (0.11 g, 3.7 mmol), 1,4-dioxane (5 ml) and concentrated hydrochloric acid solution (1.3 ml) was heated at reflux for 80 h. The reaction mixture was diluted with ethyl acetate (100 ml) and washed with 0.5 M aqueous sodium hydroxide solution. The aqueous layer was extracted with ethyl acetate (100 ml). The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. Flash chromatography of the crude product with dichloromethane/methanol as eluent gave the title compound (0.053 g, 50%) as yellow solid. MS m/e: 204 (M+H+).

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 80 h
  3. washwashed with 0.5 M aqueous sodium hydroxide solution
  4. extractionThe aqueous layer was extracted with ethyl acetate (100 ml)
  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-fbe554137b2e49738e06414efffe3b1d
出典データセット
uspto-grants-2014_03
特許番号
US08664216B2

関連ノート

読み込み中…