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

HRID 1182731

반응식

HRID 1182731 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-fbe554137b2e49738e06414efffe3b1d
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08664216B2

연결된 노트

불러오는 중…