Methylamine → N-methyl-10,11-dihydro5H-dibenzo[a,d]cyclohepten-5-imine

HRID 1076069노트

반응식

HRID 1076069 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.[CH3:17][NH2:18].C(=O)(O)[O-].[Na+]>C1C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[CH3:17][N:18]=[C:6]1[C:5]2[CH:4]=[CH:3][CH:2]=[CH:1][C:11]=2[CH2:10][CH2:9][C:8]2[CH:12]=[CH:13][CH:14]=[CH:15][C:7]1=2

참가 물질

6

반응물 3

HCID 6329MethylamineHCID 14589DibenzosuberoneHCID 516892Sodium Bicarbonate

생성물 1

HCID 21541752N-methyl-10,11-dihydro5H-dibenzo[a,d]cyclohepten-5-imine수율 90%

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 241Benzene용매2회

실험 절차

A solution of 52.5 g of titanium tetrachloride in 300 ml of anhydrous benzene is added slowly, under nitrogen, to a stirred, cooled (ice-bath) mixture of 100 g of 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one, 103 g of methylamine and 1200 ml of anhydrous benzene. After stirring at room temperature for 12 days the mixture is cooled, treated with concentrated aqueous sodium bicarbonate solution and filtered through Celite. The layers of the filtrate are separated, and the benzene layer is dried with magnesium sulfate. Removal of the solvent and crystallization of the residue from 200 ml of hexane gives 95.6 g (88% yield) of N-methyl-10,11-dihydro5H-dibenzo[a,d]cyclohepten-5-imine, mp 89°-90°. An analytical sample (hexane) also had mp 89°-90°. Nmr spectrum (in CDCl3): multiplets at τ 2.3-3.2 (8H) and 6.8-7.2 (4H) and singlet at 6.7 (3H).

후처리

  1. temperaturecooled
  2. temperatureis cooled
  3. filtrationfiltered through Celite
  4. customThe layers of the filtrate are separated
  5. dry with materialthe benzene layer is dried with magnesium sulfate
  6. customRemoval of the solvent and crystallization of the residue from 200 ml of hexane

출처 및 근거

ORD 기록
ord-8ff2a7a658544ba3ba66873a786c9fb5
출처 데이터셋
uspto-grants-1976_05
특허 번호
US03954865

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