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

HRID 917945

Reaktionsgleichung

Reaktionsgleichung von HRID 917945
[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

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

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.).

Aufarbeitung

  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.)

Quellen und Nachweise

ORD-Eintrag
ord-4d3f62cca67a4663aab24141d04cde36
Quelldatensatz
uspto-grants-1976_07
Patentnummer
US03968217

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