Water → N-cyclopropyl-10,11-dihydro-5H-dibenzo-[a,d]cyclohepten-5-imine

HRID 1076070ノート

反応式

HRID 1076070 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[C:6](=O)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH:17]1([NH2:20])[CH2:19][CH2:18]1.O>CN(C)P(N(C)C)(N(C)C)=O.C1C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[CH:17]1([N:20]=[C:6]2[C:5]3[CH:4]=[CH:3][CH:2]=[CH:1][C:11]=3[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]2=3)[CH2:19][CH2:18]1

参加物

7

反応物 3

HCID 962WaterHCID 14589DibenzosuberoneHCID 69828Cyclopropylamine

生成物 1

HCID 21541754N-cyclopropyl-10,11-dihydro-5H-dibenzo-[a,d]cyclohepten-5-imine

試薬・触媒・溶媒 3

HCID 24193Titanium Tetrachloride触媒HCID 241Benzene溶媒2 回HCID 12679Hexamethylphosphoramide溶媒

実験手順

To a solution of 5 g of 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one and 20 g of cyclopropylamine in 25 ml of hexamethylphosphoramide is added, with cooling, during 30 minutes, a solution of 1.7 ml of titanium tetrachloride in 10 ml of anhydrous benzene. After stirring at room temperature for 2 weeks, benzene (50 ml) and water (50 ml) are added, with cooling. The mixture is filtered, the layers of the filtrate are separated, and the aqueous phase is extracted with 50 ml of benzene. The combined aqueous phases are washed with 5% aqueous sodium bicarbonate solution (25ml) and water (3 × 25 ml) and dried with magnesium sulfate. The solvent is removed, and the residue is shortpath distilled at a bath temperature of 145°-150° (0.3 micron) to give N-cyclopropyl-10,11-dihydro-5H-dibenzo-[a,d]cyclohepten-5-imine as a solid. Nmr spectrum (in CDCl3): multiplets at τ 2.3-3.0 (8H) 6.6-7.2 (5H) and 8.2-9.4 (4H).

後処理

  1. temperaturewith cooling, during 30 minutes
  2. temperaturewith cooling
  3. filtrationThe mixture is filtered
  4. customthe layers of the filtrate are separated
  5. extractionthe aqueous phase is extracted with 50 ml of benzene
  6. washThe combined aqueous phases are washed with 5% aqueous sodium bicarbonate solution (25ml) and water (3 × 25 ml)
  7. dry with materialdried with magnesium sulfate
  8. customThe solvent is removed
  9. distillationthe residue is shortpath distilled at a bath temperature of 145°-150° (0.3 micron)

出典と根拠

ORDレコード
ord-e3c5274115914f15bcc558d7898fa0bd
出典データセット
uspto-grants-1976_05
特許番号
US03954865

反応ノート

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