Hydrochloric Acid → 2-Methyl-4-morpholino-5-fluoroindoline

HRID 434679

Reaction equation

HRID 434679 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[C:8]([N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)[C:7]([F:17])=[CH:6][CH:5]=2.[Sn].Cl>C(O)(=O)C>[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([F:17])[C:8]=2[N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[NH:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5352426Tin atomHCID 202589922-Methyl-4-morpholino-5-fluoroindole

Product 1

HCID 202589752-Methyl-4-morpholino-5-fluoroindolineYield 53.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

2-Methyl-5-fluoro-4-morpholinoindole (138 g) was dissolved in 1.5 l of acetic acid. To this solution was added 200 g of metal tin and the mixture was under reflux of acetic acid. During reflux 1.5 l of concentrated hydrochloric acid was added dropwise in 1 hour. After completion of addition, the mixture was allowed to react for 2 hours at the same temperature as above. After completion of reaction, the solvent was distilled off under reduced pressure. To the residue was added 1 l of water and the solution was adjusted to pH 13 with a 20% aqueous sodium hydroxide solution followed by adding 1 l of ether. After stirring insoluble substances were removed by filtration. An ether layer was separated from the filtrate and dried over anhydrous potassium carbonate. Removal of ether by distillation gave 75 g of 2-methyl-4-morpholino-5-fluoroindoline.

Workup

  1. additionwas added dropwise in 1 hour
  2. additionAfter completion of addition
  3. customto react for 2 hours at the same temperature as above
  4. customAfter completion of reaction
  5. distillationthe solvent was distilled off under reduced pressure
  6. additionTo the residue was added 1 l of water
  7. additionby adding 1 l of ether
  8. customwere removed by filtration
  9. customAn ether layer was separated from the filtrate
  10. dry with materialdried over anhydrous potassium carbonate
  11. customRemoval of ether
  12. distillationby distillation

Sources & evidence

ORD record
ord-c36e32c2ba00439888889127fa986114
Source dataset
uspto-grants-1983_08
Patent number
US04399134

Linked notes

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