Water → Cyclopropyl-{6-[1-(4-fluoro-phenyl)-1h-indol-5-yloxy]-hexyl}-methyl-amine

HRID 1633616Notes

Reaction equation

HRID 1633616 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)[CH:13]=[CH:12]2.[H-].[Na+].[CH3:27][CH2:28]OCC.O.[CH3:33][N:34]([CH:36]=O)C>>[CH:36]1([N:34]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH:13]=[CH:12]3)[CH3:33])[CH2:28][CH2:27]1

Participants

6

Reactant 5

HCID 962WaterHCID 3283Diethyl EtherHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 117496125-(6-Bromo-hexyloxy)-1-(4-fluoro-phenyl)-1H-indole

Product 1

HCID 18679440Cyclopropyl-{6-[1-(4-fluoro-phenyl)-1h-indol-5-yloxy]-hexyl}-methyl-amineYield 73%

Procedure

195 mg (0.5 mmol) 5-(6-Bromo-hexyloxy)-1-(4-fluoro-phenyl)-1H-indole in 2.5 ml DMF were treated with 185 mg (1 mmol) cyclopropyl-methyl amine·CF3CO2H and 96 mg (2 mmol, 50% in mineral oil) NaH at RT for 2 h and at 60° C. for 3 h. At RT, ether and water were added and the inorganic phase was extracted with ether. The combined organic phases were washed with water, dried over Na2SO4 and evaporated. Purification on silica gel with hexane/ether 1:1 yielded 140 mg (73%) Cyclopropyl-{6-[1-(4-fluoro-phenyl)-1H-indol-5-yloxy]-hexyl}-methyl-amine as light yellow oil, MS: 381 (MH+).

Workup

  1. extractionthe inorganic phase was extracted with ether
  2. washThe combined organic phases were washed with water
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customPurification on silica gel with hexane/ether 1:1

Sources & evidence

ORD record
ord-938d48b6940f48ac8d2b9d98ce7707bd
Source dataset
uspto-grants-2003_01
Patent number
US06503907B2

Reaction notes

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