(+/-)-1-Benzoyl-6-bromo-4-(di-n-propylamino)hexahydrobenz[cd]indole → 1-Benzoyl-6-cyano-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole

HRID 263509ノート

反応式

HRID 263509 の反応式
[C:1]([N:9]1[C:17]2[CH:16]=[CH:15][CH:14](Br)[CH:13]3[CH2:19][CH:20]([N:22]([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25])[CH2:21][CH:11]([C:12]=23)[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29]([Cu])#[N:30]>CN(C=O)C.O.C(Cl)Cl.[Cu]I>[C:1]([N:9]1[C:17]2[CH:16]=[CH:15][C:14]([C:29]#[N:30])=[C:13]3[CH2:19][CH:20]([N:22]([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25])[CH2:21][CH:11]([C:12]=23)[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 2

HCID 67742868(+/-)-1-Benzoyl-6-bromo-4-(di-n-propylamino)hexahydrobenz[cd]indoleHCID 178418546HCID 178418546、化合物

生成物 1

HCID 148320451-Benzoyl-6-cyano-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole収率 82.6%

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
140 °C

実験手順

To a solution of (±)-1-benzoyl-6-bromo-4-(di-n-propylamino)hexahydrobenz[cd]indole (5.5 g, 12.5 mmol) in DMF (100 mL) under a N2 atmosphere was added 3.4 g (37.5 mmol) of CuCN and 7.1 g (37.5 mmol) of CuI. The reaction mixture was then stirred at 140° C. for 6 hr. The reaction mixture was poured onto ice, diluted with water, CH2Cl2 added and stirred for 30 minutes. The mixture was filtered through a Celite pad and the filtrate was extracted twice with CH2Cl2. The organic solution was washed twice with saturated NaCl solution. The CH2Cl2 solution was dried over MgSO4 and then evaporated to provide 4 g of a solid. Chromatography of this crude product over silica gel with 1:19 MeOH/CH2Cl2 as eluent gave 3 g (62%) of product. mp=122°-124° C.

後処理

  1. additionThe reaction mixture was poured onto ice
  2. additionadded
  3. stirringstirred for 30 minutes
  4. filtrationThe mixture was filtered through a Celite pad
  5. extractionthe filtrate was extracted twice with CH2Cl2
  6. washThe organic solution was washed twice with saturated NaCl solution
  7. dry with materialThe CH2Cl2 solution was dried over MgSO4
  8. customevaporated

出典と根拠

ORDレコード
ord-b923ed98ce8a4384bb0604593ef3c962
出典データセット
uspto-grants-1997_07
特許番号
US05643930

反応ノート

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