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

HRID 917945

反応式

HRID 917945 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回HCID 8058Hexane溶媒

実験手順

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.).

後処理

  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.)

出典と根拠

ORDレコード
ord-4d3f62cca67a4663aab24141d04cde36
出典データセット
uspto-grants-1976_07
特許番号
US03968217

関連ノート

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