Sodium Sulfate → 7-Fluorotryptamine

HRID 1666898Notes

Reaction equation

HRID 1666898 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:16]=1[NH:15][CH:14]=[C:13]2[CH:17]=[CH:18][N+:19]([O-])=O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[F:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:16]=1[NH:15][CH:14]=[C:13]2[CH2:17][CH2:18][NH2:19]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 67443309HCID 67443309, compound

Product 1

HCID 27693627-FluorotryptamineYield 12.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Combine lithium aluminum hydride (12.8 g; 336.1 mmol) and 0° C. anhydrous tetrahydrofuran (160 mL). Cool resulting exotherm to 0° C. Add 7-fluoro-3-(2-nitrovinyl)-1H-indole (11.55 g, 56.0 mmol) in anhydrous THF (200 mL) dropwise. After 30 min, warm to ambient temperature. After 4 hours, cool to 0° C. and add saturated sodium sulfate solution (35 mL) dropwise. Filter the solids and wash with THF and ethyl acetate. Concentrate the filtrate and dissolve the residue in methylene chloride. Filter the precipitate to give 1.26 g of product as brown crystals. Concentrate the filtrate and chromatograph on silica gel eluting with 5%, 7%, 10% 2N ammonia in methanol/methylene chloride to give product: MS (m/e): 179 (M+1), 177 (M−1); Calculated for C10H11FN2: Calcd: C, 67.40; H, 6.22; N, 15.72. Found: C, 67.06; H, 6.11; N, 15.48.

Workup

  1. temperatureCool
  2. customresulting exotherm to 0° C
  3. waitAfter 4 hours
  4. temperaturecool to 0° C.
  5. filtrationFilter the solids
  6. washwash with THF and ethyl acetate
  7. concentrationConcentrate the filtrate
  8. dissolutiondissolve the residue in methylene chloride
  9. filtrationFilter the precipitate

Sources & evidence

ORD record
ord-fc385479db30486d87ff6596f2c150fd
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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