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

HRID 1076069

反応式

HRID 1076069 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.[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

参加物

6

反応物 3

HCID 6329MethylamineHCID 14589DibenzosuberoneHCID 516892Sodium Bicarbonate

生成物 1

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

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 241Benzene溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8ff2a7a658544ba3ba66873a786c9fb5
出典データセット
uspto-grants-1976_05
特許番号
US03954865

関連ノート

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