HCID 13324711, compound → HCID 13324728, compound

HRID 371494Notes

Reaction equation

HRID 371494 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[C:20]#[N:21])[CH:12]=[CH:11]2>O1CCCC1>[ClH:7].[Cl:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([C:17]1[CH:18]=[C:19]([CH2:20][NH2:21])[CH:22]=[CH:23][CH:24]=1)[CH:12]=[CH:11]2

Participants

4

Reactant 2

HCID 13324711HCID 13324711, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13324728HCID 13324728, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred mixture of 1.67 g of lithium aluminum hydride in 100 ml of dry tetrahydrofuran (THF), kept at 0°-5° C. under nitrogen, was added dropwise a solution of 5.60 g (0.022 mole) of 3-(5-chloro-1-indolyl)benzonitrile of Example 6a in 150 ml of THF. The mixture was stirred 1 hour more at 0° C., 1 hour at room temperature, and then refluxed for 5 hours. After cooling to 0° C., the reaction was quenched by slow and cautious addition of a solution of 25 ml of water in 25 ml of THF. The resulting mixture was stirred 1 hour at room temperature before filtering to remove the inorganic salts. The filtrate was concentrated to an oily residue which was partitioned between 250 ml of dichloromethane and 250 ml of water. The organic phase was separated and extracted twice more with water before drying over Na2SO4 and concentrating to an oil (5.8 g). This was dissolved in 20 ml of absolute ethanol and the stirred solution treated with 100 ml of ethereal hydrogen chloride. The salt was collected and found to weigh 5.2 g (81% overall yield) m.p. 195° C.-sinter, 220°-228° C. melting. Recrystallization from boiling ethanol (charcoal) furnished 2.4 g (37% yield) of 3-(5-chloro-1-indolyl)benzenemethanamine hydrochloride, m.p. 230°-233° C.

Workup

  1. customkept at 0°-5° C. under nitrogen
  2. temperaturerefluxed for 5 hours
  3. temperatureAfter cooling to 0° C.
  4. customthe reaction was quenched by slow and
  5. additioncautious addition of a solution of 25 ml of water in 25 ml of THF
  6. stirringThe resulting mixture was stirred 1 hour at room temperature
  7. filtrationbefore filtering
  8. customto remove the inorganic salts
  9. concentrationThe filtrate was concentrated to an oily residue which
  10. customwas partitioned between 250 ml of dichloromethane and 250 ml of water
  11. customThe organic phase was separated
  12. extractionextracted twice more with water
  13. dry with materialbefore drying over Na2SO4
  14. concentrationconcentrating to an oil (5.8 g)
  15. dissolutionThis was dissolved in 20 ml of absolute ethanol
  16. additionthe stirred solution treated with 100 ml of ethereal hydrogen chloride
  17. customThe salt was collected
  18. custom5.2 g (81% overall yield) m.p. 195° C.-sinter, 220°-228° C.
  19. customRecrystallization

Sources & evidence

ORD record
ord-75e95716ea0d4e4cac8d42ff758e7442
Source dataset
uspto-grants-1985_07
Patent number
US04532333

Reaction notes

Loading…