Decalin → 5-(4-(2-hydroxyethyl)phenyl)-5H-dibenz[b,f]azepine

HRID 1815610노트

반응식

HRID 1815610 반응식
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.I[C:17]1[CH:25]=[CH:24][C:20]([CH2:21][CH2:22][OH:23])=[CH:19][CH:18]=1.[OH-].[K+].C1C2C(CCCC2)CCC1>[Cu].C(Cl)(Cl)Cl>[OH:23][CH2:22][CH2:21][C:20]1[CH:24]=[CH:25][C:17]([N:6]2[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH:9]=[CH:10][C:11]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]2=3)=[CH:18][CH:19]=1

참가 물질

7

반응물 4

HCID 7044DecalinHCID 9212Dibenz(b,f)azepineHCID 14797Potassium HydroxideHCID 30407702-(4-Iodophenyl)ethan-1-ol

생성물 1

HCID 130082485-(4-(2-hydroxyethyl)phenyl)-5H-dibenz[b,f]azepine수율 30%

시약·촉매·용매 2

HCID 23978Copper촉매HCID 6212Chloroform용매

실험 절차

A mixture of 8.7 g (45 mmol) of 5H-dibenz[b,f]azepine, 12.4 g (50 mmol) of p-iodophenethyl alcohol, 2.8 g (50 mmol) of potassium hydroxide, 4. 8 g (75 mmol) of copper powder, and 20 ml of decalin was heated at an external temperature of 200° C. while stirring in a nitrogen stream for 40 hours. The reaction mixture was cooled nearly to room temperature, chloroform was added thereto, followed by filtration using Celite to remove any insoluble matter. The filtrate was concentrated. To remove decalin, n-hexane was added to the residue, followed by filtration. The filter cake was reprecipitated in methanol, and the resulting crude product was purified by silica gel column chromatography to give 4.2 g (30%) of 5-(4-(2-hydroxyethyl)phenyl)-5H-dibenz[b,f]azepine.

후처리

  1. filtrationfollowed by filtration
  2. customto remove any insoluble matter
  3. concentrationThe filtrate was concentrated
  4. customTo remove decalin, n-hexane
  5. additionwas added to the residue
  6. filtrationfollowed by filtration
  7. customThe filter cake was reprecipitated in methanol
  8. customthe resulting crude product was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-6f51176524f446d89081b4557b98c0a5
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06878822B2

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