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

HRID 1633641Notes

Reaction equation

HRID 1633641 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][CH2:20][CH2:21]OS(C)(=O)=O)=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1.[CH2:27]([CH2:30][NH2:31])[CH:28]=C.[CH3:32]N(C=O)C>>[CH2:30]([N:31]([CH2:21][CH2:20][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)[CH3:32])[CH:27]=[CH2:28]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 4437323-Buten-1-amineHCID 86585585Methanesulfonic acid 5-[1-(4-fluoro-phenyl)-1H-indol-5-yl]-pentyl ester

Product 1

HCID 18679496Allyl-{5-[1-(4-fluoro-phenyl)-1H-indol-5-yl]-pentyl}-methyl-amineYield 98%

Procedure

130 mg (0.26 mmol) Methanesulfonic acid 5-[1-(4-fluoro-phenyl)-1H-indol-5-yl]-pentyl ester and 0.5 ml (5.2 mmol) N-allylmethylamine in 0.5 ml DMF were stirred at 60° C. for 2 h. The solution was concentrated and dissolved in water and CH2Cl2. 2M NaOH was added and the inorganic phase was extracted with CH2Cl2. The combined organic phases were washed with water and dried over Na2SO4. Column chromatography with CH2Cl2/MeOH 19:1 yielded 90 mg (98%) Allyl-{5-[1-(4-fluoro-phenyl)-1H-indol-5-yl]-pentyl}-methyl-amine as orange oil, MS: 351(MH+).

Workup

  1. concentrationThe solution was concentrated
  2. dissolutiondissolved in water
  3. addition2M NaOH was added
  4. extractionthe inorganic phase was extracted with CH2Cl2
  5. washThe combined organic phases were washed with water
  6. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-1a2b5dfffb874cdf884c66a67247e2e5
Source dataset
uspto-grants-2003_01
Patent number
US06503907B2

Reaction notes

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