Toluene → 5-(3-Chloropropyl)-10,11-dihydro-5H-dibenz[b,f]azepine

HRID 917945

반응식

HRID 917945 반응식
[CH:1]1[C:11]2[CH2:10][CH2:9][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.C([Li])CCC.Br[CH2:22][CH2:23][CH2:24][Cl:25].C1(C)C=CC=CC=1>CCOCC.CCCCCC>[Cl:25][CH2:24][CH2:23][CH2:22][N:6]1[C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[CH2:9][CH2:10][C:11]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]1=2

참가 물질

7

반응물 4

HCID 1140TolueneHCID 80061-Bromo-3-chloropropaneHCID 10308IminodibenylHCID 178418339Butyllithium

생성물 1

HCID 2867795-(3-Chloropropyl)-10,11-dihydro-5H-dibenz[b,f]azepine

시약·촉매·용매 2

HCID 3283Diethyl Ether용매2회HCID 8058Hexane용매

실험 절차

A solution of 10,11-dihydro-5H-dibenz[b,f]azepine (19.5 gms.; 0.10 moles) in dry ether was added to a solution of 7.7 gms. (0.12 mole) of butyl lithium in hexane. The stirred solution was warmed for approximately one hour and then 31.0 gms. (0.20 mole) of bromopropylchloride in ether was added and the resulting mixture heated at reflux for 16 hours. Aliquot analysis showed no reaction had taken place. Approximately one liter of toluene was added to the reaction mixture, lower boiling solvents were removed by distillation and the reaction mixture heated at reflux with stirring for 12 hours. On working up the reaction mixture, there was obtained 7.0 gms. of 5-(3-chloropropyl)-10,11-dihydro-5H-dibenz[b,f]azepine which distilled at 150°-153°C. (0.03 mm.). An additional 6.0 gms. of impure material which contained approximately 15% of unreacted 10,11-dihydro-5H-dibenz[b,f]azepine was obtained which distilled at 140°-150°C. (0.03 mm.).

후처리

  1. temperatureThe stirred solution was warmed for approximately one hour
  2. temperaturethe resulting mixture heated
  3. temperatureat reflux for 16 hours
  4. customwere removed by distillation
  5. temperaturethe reaction mixture heated
  6. temperatureat reflux
  7. customthere was obtained 7.0 gms
  8. distillationof 5-(3-chloropropyl)-10,11-dihydro-5H-dibenz[b,f]azepine which distilled at 150°-153°C. (0.03 mm.)
  9. customwas obtained which
  10. distillationdistilled at 140°-150°C. (0.03 mm.)

출처 및 근거

ORD 기록
ord-4d3f62cca67a4663aab24141d04cde36
출처 데이터셋
uspto-grants-1976_07
특허 번호
US03968217

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