(+/-)-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 233778노트

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HRID 233778 반응식
[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

참가 물질

7

반응물 2

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

생성물 1

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

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

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온도
140 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3c01e96c60ff48bfa7b9e8faa80b340d
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05594019

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