Dibenzosuberol → Oxitriptyline

HRID 1900249

反応式

HRID 1900249 の反応式
[H-].[Na+].[CH2:3]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]([OH:18])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]1.Cl[CH2:20][C:21]([N:23]([CH3:25])[CH3:24])=[O:22]>CCCCCC.CCOCC>[CH:16]1[C:17]2[CH2:3][CH2:4][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=3[CH:11]([O:18][CH2:20][C:21]([N:23]([CH3:25])[CH3:24])=[O:22])[C:12]=2[CH:13]=[CH:14][CH:15]=1

参加物

6

反応物 3

HCID 14588DibenzosuberolHCID 24758Sodium hydrideHCID 758862-chloro-N,N-dimethylacetamide

生成物 1

HCID 34624Oxitriptyline収率 72.3%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒3 回HCID 8058Hexane溶媒

実験手順

Washed sodium hydride (2.6 g, 64.6 mmol, 60 weight % in oil) two times with hexane under a nitrogen atmosphere. Added 50 mL of dry ether, and then added dibenzosuberol (13.6 g, 64.6 mmol) dissolved in 30 mL of dry ether followed by 2-chloro-N,N-dimethylacetamide (7.8 g, 64.6 mmol) dissolved in 20 mL of dry ether. Stirred at room temperature for 16 hours. Added water, and separated layers. Evaporated the organic solution, and triturated the residue with carbon tetrachloride and hexane. Filtered the white solid to give 13.79 g (72% yield) of 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl-oxy-N,N-dimethylacetamide.

後処理

  1. customAdded water, and separated layers
  2. customEvaporated the organic solution
  3. customtriturated the residue with carbon tetrachloride and hexane
  4. filtrationFiltered the white solid

出典と根拠

ORDレコード
ord-ba38d220116b4c5a8607969808d79758
出典データセット
uspto-grants-1996_11
特許番号
US05574173

関連ノート

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