Dimethylformamide → Allyl-{4-[1-(4-fluoro-phenyl)-1H-indol-5-yloxy]-butyl}-methyl-amine

HRID 1633622Notes

Reaction equation

HRID 1633622 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[CH:11]=[CH:10]2.[CH2:23]([CH2:26][NH2:27])[CH:24]=C.[CH3:28]N(C=O)C>>[CH2:26]([N:27]([CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[CH:11]=[CH:10]2)[CH3:28])[CH:23]=[CH2:24]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 4437323-Buten-1-amineHCID 186794275-(4-Bromo-butoxy)-1-(4-fluoro-phenyl)-1H-indole

Product 1

HCID 10154999Allyl-{4-[1-(4-fluoro-phenyl)-1H-indol-5-yloxy]-butyl}-methyl-amineYield 77%

Conditions

Temperature
60 °C

Procedure

To 160 mg (0.44 mmol) 5-(4-Bromo-butoxy)-1-(4-fluoro-phenyl)-1H-indole in 2 ml DMF were added 0.5 ml (5.2 mmol) N-allylmethylamine and the solution was heated to 60° C. for 30 min. After concentration in vacuo, the residue was dissolved in water and ether. 2M NaOH was added, and the inorganic phase was extracted with ether, the combined organic phases were washed with water and dried over Na2SO4. Column chromatography on silica gel with CH2Cl2/MeOH 9:1 yielded 120 mg (77%) Allyl-{4-[1-(4-fluoro-phenyl)-1H-indol-5-yloxy]-butyl}-methyl-amine as yellow oil, MS: 353 (MH+).

Workup

  1. concentrationAfter concentration in vacuo
  2. dissolutionthe residue was dissolved in water
  3. addition2M NaOH was added
  4. extractionthe inorganic phase was extracted with ether
  5. washthe combined organic phases were washed with water
  6. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-6def8dfaaadb4e64892c7133b0ac5577
Source dataset
uspto-grants-2003_01
Patent number
US06503907B2

Reaction notes

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