Sodium Hydroxide → 5-Chlorotryptamine

HRID 1666883Notes

Reaction equation

HRID 1666883 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Al+3].[Cl-].[Cl-].[Cl-].[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][CH:16]=[C:15]2[C:21](=O)[C:22]([NH2:24])=O.[OH-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+].CCOCC.Cl>C1COCC1.CCOCC>[Cl:11][C:12]1[CH:13]=[C:14]2[C:18]([NH:17][CH:16]=[C:15]2[CH2:21][CH2:22][NH2:24])=[CH:19][CH:20]=1

Participants

9

Reactant 6

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 6451240Aluminum(III) ChlorideHCID 10953452Ether hydrochlorideHCID 21071422HCID 21071422, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 773795-Chlorotryptamine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
5 °C

Procedure

Cool to 5° C., a suspension of LiAlH4 (40.97 g) in THF (700 ml). Add a solution of AlCl3 (53.9 g, 0.40 mole) to THF (645 ml) over about 30 minutes while maintaining the temperature at about 5° C. and 10° C. Add (2-(5-chloro-1H-Indol-3-yl)-2-oxo-acetamide (20 g, 0.09 mole) in THF (900 ml) while maintaining the temperature at between 5° C. and 7.5° C. When the addition is complete warm to room temperature. Stir overnight and then cool to 7° C. and slowly add a solution of NaOH 50% (342 g, 4.28 mol). After stirring for about 1 hour, add anhydrous Na2SO4 (30 g) and filter the suspension on a celite bed. Evaporate the filtrate to dryness to give an oil. Combine the and Et2O (500 mL) and add a solution of Et2O/HCl 4.5N (15 mL) at room temperature to give a solid. Stir the suspension at room temperature for 1 hour, filter, and wash with 50 mL Et2O, dry under vacuum at 50° C. to give the hydrochloride of the title compound.

Workup

  1. temperaturewhile maintaining the temperature at about 5° C.
  2. custom10° C
  3. temperaturewhile maintaining the temperature at between 5° C. and 7.5° C
  4. additionWhen the addition
  5. temperatureis complete warm to room temperature
  6. temperaturecool to 7° C.
  7. stirringAfter stirring for about 1 hour
  8. filtrationfilter the suspension on a celite bed
  9. customEvaporate the filtrate to dryness
  10. customto give an oil
  11. customto give a solid
  12. stirringStir the suspension at room temperature for 1 hour
  13. filtrationfilter
  14. washwash with 50 mL Et2O
  15. customdry under vacuum at 50° C.

Sources & evidence

ORD record
ord-acf6e7b916154d2ea06faae93e8b3ec2
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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