Dimethylformamide → HCID 18679518, compound

HRID 1633642Notes

Reaction equation

HRID 1633642 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH2:17][CH2:18][CH2:19]OS(C)(=O)=O)=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1.[CH2:25]([CH2:28][NH2:29])[CH:26]=C.[CH3:30]N(C=O)C>>[CH2:28]([N:29]([CH2:19][CH2:18][CH2:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[N:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH:9]=[CH:10]2)[CH3:30])[CH:25]=[CH2:26]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 4437323-Buten-1-amineHCID 86585586Methanesulfonic acid 3-[1-(4-fluoro-phenyl)-1H-indol-5-yl]-propyl ester

Product 1

HCID 18679518HCID 18679518, compoundYield 76%

Procedure

150 mg (0.43 mmol) Methanesulfonic acid 3-[1-(4-fluoro-phenyl)-1H-indol-5-yl]-propyl ester and 0.5 ml N-allylmethylamine in 1 ml DMF were stirred at 60° C. for 1 h. The solution was concentrated and dissolved in water, ether and 0.5M NaOH was added. The inorganic phase was extracted with ether and the combined organic phases were washed with water and dried over Na2SO4. Column chromatography with CH2Cl2/MeOH 19:1 yielded 105 mg (76%) Allyl-{3-[1-(4-fluoro-phenyl)-1H-indol-5-yl]-propyl}-methyl-amine as light brown oil, MS: 323 (MH+).

Workup

  1. concentrationThe solution was concentrated
  2. dissolutiondissolved in water
  3. additionether and 0.5M 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-0e3f17b257dc482d90c595d076790cee
Source dataset
uspto-grants-2003_01
Patent number
US06503907B2

Reaction notes

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