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

HRID 1076070노트

반응식

HRID 1076070 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[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

참가 물질

7

반응물 3

HCID 962WaterHCID 14589DibenzosuberoneHCID 69828Cyclopropylamine

생성물 1

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

시약·촉매·용매 3

HCID 24193Titanium Tetrachloride촉매HCID 241Benzene용매2회HCID 12679Hexamethylphosphoramide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-e3c5274115914f15bcc558d7898fa0bd
출처 데이터셋
uspto-grants-1976_05
특허 번호
US03954865

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