(+/-)-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 1488525Notes

Reaction equation

HRID 1488525 reaction equation
[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.ClCl.[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

Participants

7

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 24526ChlorineSolvent

Conditions

Temperature
140 °C

Procedure

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, CH2 Cl2 added and stirred for 30 minutes. The mixture was filtered through a Celite pad and the filtrate was extracted twice with CH2 Cl2. 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.

Workup

  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 CH2 Cl2
  6. washThe organic solution was washed twice with saturated NaCl solution
  7. dry with materialThe CH2Cl2 solution was dried over MgSO4
  8. customevaporated

Sources & evidence

ORD record
ord-93657bf568e04ceeb63aec39b4c6a789
Source dataset
uspto-grants-1997_10
Patent number
US05674884

Reaction notes

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