Hydrogen Bromide → 1-Benzyl-4-(6-hydroxynaphth-2-yl)-1,2,3,6-tetrahydropyridine

HRID 380546노트

반응식

HRID 380546 반응식
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](O)([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([O:24]C)[CH:20]=3)[CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br.[OH-].[Na+]>C(O)(=O)C>[CH2:1]([N:8]1[CH2:9][CH:10]=[C:11]([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([OH:24])[CH:20]=3)[CH:15]=2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 183652491-Benzyl-4-hydroxy-4-(6-methoxynaphth-2-yl)piperidine

생성물 1

HCID 177857841-Benzyl-4-(6-hydroxynaphth-2-yl)-1,2,3,6-tetrahydropyridine수율 63%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A solution of 1.0 gm (2.9 mMol) 1-benzyl-4-hydroxy-4-(6-methoxynaphth-2-yl)piperidine and 0.65 mL (5.8 mMol) 48% hydrobromic acid in 10 mL acetic acid was heated at reflux for 18 hours. The reaction mixture was cooled to room temperature, neutralized with 5N sodium hydroxide, and extracted well with ethyl acetate. The organic extracts were combined, washed with saturated aqueous sodium chloride, dried over sodium sulfate, and concentrated under reduced pressure. The residual solid was suspended in a mixture of ethyl acetate and hexane and the suspension sonicated. The suspension was then filtered to provide 0.57 gm (63%) of the desired compound as a grey solid.

후처리

  1. temperatureat reflux for 18 hours
  2. extractionextracted well with ethyl acetate
  3. washwashed with saturated aqueous sodium chloride
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionThe residual solid was suspended in a mixture of ethyl acetate and hexane
  7. customthe suspension sonicated
  8. filtrationThe suspension was then filtered

출처 및 근거

ORD 기록
ord-da0803fc86fc4811a83bc0351cb83b18
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06303627B1

반응 노트

불러오는 중…