(+/-)-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 1377797Notes

Reaction equation

HRID 1377797 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.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

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 6344DichloromethaneSolvent

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, 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 MeOHH2Cl2 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 CH2Cl2
  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-40e053d276aa49b88b552ff9a61dc6b5
Source dataset
uspto-grants-1997_09
Patent number
US05665758

Reaction notes

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