4-Methylmorpholine → N-(Benzyloxycarbonyl)-5-fluorotryptamine

HRID 1079374Notes

Reaction equation

HRID 1079374 reaction equation
[F:1][C:2]1[CH:13]=[C:12]2[C:5]([NH:6][CH:7]=[C:8]2[CH2:9][CH2:10][NH2:11])=[CH:4][CH:3]=1.CN1CCOCC1.[CH2:21]([O:28][C:29](Cl)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C=O)C.O>[CH2:21]([O:28][C:29]([NH:11][CH2:10][CH2:9][C:8]1[C:12]2[C:5](=[CH:4][CH:3]=[C:2]([F:1])[CH:13]=2)[NH:6][CH:7]=1)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 79724-MethylmorpholineHCID 10387Benzyl chloroformateHCID 1646825-Fluorotryptamine

Product 1

HCID 9948665N-(Benzyloxycarbonyl)-5-fluorotryptamineYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 0.83 g (4-6 mmol) of 5-fluorotryptamine and 0.48 g (0.55 mL, 5 mmol) of n-methylmorpholine in 10 mL of DMF at 0° C. was added dropwise 0.72 mL (5 mmol) of benzylchloroformate. The reaction mixture was allowed to stir at 0° C. under argon. After 1.5 hours of stirring, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic extracts were washed with saturated sodium chloride, dried over anhydrous Na2SO4, and concentrated under vacuum. The resulting residue was purified by flash chromatography using hexane:ethyl acetate (2:1) as an eluent to yield 1 g (68%) of N-(Benzyloxycarbonyl)-5-fluorotryptamine as a white solid. mp 104°-105° C.

Workup

  1. stirringAfter 1.5 hours of stirring
  2. extractionextracted with ethyl acetate
  3. washThe organic extracts were washed with saturated sodium chloride
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under vacuum
  6. customThe resulting residue was purified by flash chromatography

Sources & evidence

ORD record
ord-88101240adff4730b92710d9ca6a6244
Source dataset
uspto-grants-1996_12
Patent number
US05580878

Reaction notes

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