Methanol → HCID 21071559, compound

HRID 1666819Notes

Reaction equation

HRID 1666819 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[F:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:19]=1[C:15]([CH2:16][CH2:17][NH2:18])=[CH:14][NH:13]2.CO.CCOCC>C(#N)C>[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[F:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:19]=1[C:15]([CH2:16][CH2:17][NH2:18])=[CH:14][NH:13]2

Participants

6

Reactant 4

HCID 887MethanolHCID 971Oxalic AcidHCID 3283Diethyl EtherHCID 209760252-(4-Fluoro-1H-indol-3-yl)ethan-1-amine

Product 1

HCID 21071559HCID 21071559, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Add dropwise oxalic acid (1.44 g, 1.2 eq.) in acetonitrile to an acetonitrile solution of 4-fluorotryptamine with vigorous stirring. Warm add MeOH to make a solution. Add Et2O to the cloud point and cool the solution in the freezer to give a solid. Collect the solid by filtration and dry in a vacuum oven overnight at 45° C. to give the title compound as a tan solid: 1H NMR (300 MHz, d6-DMSO): 3.07 (m, 4H), 6.73 (m, 1H), 7.04 (m, 1H), 7.22 (m, 2H), 11.30 (bs, 1H); MS (ES+): m/z 179 (M+H)+; (ES−): m/z 177 (M−H)−.

Workup

  1. temperatureWarm
  2. customto give a solid
  3. customCollect the solid
  4. filtrationby filtration
  5. customdry in a vacuum oven overnight at 45° C.

Sources & evidence

ORD record
ord-99c4f1479e9a4c49a3b43d8d3c132297
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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