Acetonitrile → (+)(2aR,4S)-1-benzoyl-6-bromo-4-(di-n-propylamino)1,2,2a,3,4,5-hexahydrobenz[cd]indole

HRID 1463918Notes

Reaction equation

HRID 1463918 reaction equation
[C:1]([N:9]1[C:17]2[CH:16]=[CH:15][C:14]([Br:18])=[C:13]3[CH2:19][C@@H:20]([NH2:22])[CH2:21][C@H:11]([C:12]=23)[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23](#N)[CH3:24].[C:26]([O-])([O-])=O.[K+].[K+].[CH2:32](I)[CH2:33][CH3:34]>C(Cl)Cl>[C:1]([N:9]1[C:17]2[CH:16]=[CH:15][C:14]([Br:18])=[C:13]3[CH2:19][C@@H:20]([N:22]([CH2:26][CH2:23][CH3:24])[CH2:32][CH2:33][CH3:34])[CH2:21][C@H:11]([C:12]=23)[CH2:10]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 10546231HCID 10546231, compound

Product 1

HCID 10813042(+)(2aR,4S)-1-benzoyl-6-bromo-4-(di-n-propylamino)1,2,2a,3,4,5-hexahydrobenz[cd]indoleYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2aR, 4S)-1-Benzoyl-4-amino-6-bromo-1,2,2a,3,-4,5-hexahydrobenz[cd]indole (9.82 g, 0.0275 mol) was placed in 500 ml round bottom flask equipped with a mechanical stirrer, condenser topped with a nitrogen inlet, and a thermocouple. Acetonitrile (175 ml) and K2CO3 (0.275 mol) were added, followed by the addition of propyl iodide (13.2 ml, 0.137 mol) with vigorous stirring. The reaction mixture was stirred at 75°±5° C. under nitrogen overnight. After cooling to room temperature, the reaction mixture was diluted with CH2Cl2 (200 ml) and washed successively with H2O, NaHCO3 solution, H2O, brine and dried over Na2SO4. After filtration, the volatiles were removed in vacuo to provide 11.5 g (94%) crude product. This material was then recrystallized from 95% ethanol to provide the desired product as colorless needles 9.7 g (80.0%).

Workup

  1. customequipped with a mechanical stirrer, condenser
  2. customtopped with a nitrogen inlet
  3. washwashed successively with H2O, NaHCO3 solution, H2O, brine
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration
  6. customthe volatiles were removed in vacuo
  7. customto provide 11.5 g (94%) crude product
  8. customThis material was then recrystallized from 95% ethanol

Sources & evidence

ORD record
ord-230d42ddea464448b672b735ebfc289e
Source dataset
uspto-grants-1994_04
Patent number
US05302612

Reaction notes

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