1,3-Dibromopropane → 5-(3-bromopropyl)oxy-4-propyl-N-(4-chlorophenyl)indole

HRID 342770Notes

Reaction equation

HRID 342770 reaction equation
[OH:1][C:2]1[C:3]([CH2:18][CH2:19][CH3:20])=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[CH:6]=[CH:5]2.C(=O)([O-])[O-].[K+].[K+].[Br:27][CH2:28][CH2:29][CH2:30]Br>CN(C)C=O.C(OCC)(=O)C.[Cl-].[NH4+]>[Br:27][CH2:28][CH2:29][CH2:30][O:1][C:2]1[C:3]([CH2:18][CH2:19][CH3:20])=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[CH:6]=[CH:5]2

Participants

7

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 537470165-hydroxy-4-propyl-N-(4-chlorophenyl)indole

Product 1

HCID 544467205-(3-bromopropyl)oxy-4-propyl-N-(4-chlorophenyl)indole

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 5-hydroxy-4-propyl-N-(4-chlorophenyl)indole (Step D; 500 mg, 1.75 mmol) and potassium carbonate (484 mg, 3.50 mmol) in 7 mL of dimethylformamide (DMF) was added 1,3-dibromopropane (1.77 g, 8.75 mmol). The mixture was stirred at ambient temperature for 2 hours and diluted with ethyl acetate and saturated aqueous ammonium chloride. The aqueous phase was extracted with ethyl acetate and the combined organic extracts were washed brine, dried over magnesium sulfate, filtered, concentrated in vacuo, and the crude residue was used as is in the next step.

Workup

  1. extractionThe aqueous phase was extracted with ethyl acetate
  2. washthe combined organic extracts were washed brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9a8828c43a1749eca064fb2fec71abed
Source dataset
uspto-grants-1999_01
Patent number
US05859051

Reaction notes

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