Isopropanol → 5-Bromo-N,N-Dimethyltryptamine

HRID 651715Notes

Reaction equation

HRID 651715 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11](=O)[C:12]([N:14]([CH3:16])[CH3:15])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O)(C)C.[OH-].[Na+]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][N:14]([CH3:15])[CH3:16]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 27280745-Bromo-N,N-dimethyl-α-oxo-1H-indole-3-acetamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 3602525-Bromo-N,N-DimethyltryptamineYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5-bromo-N,N-dimethyl-α-oxo-1H-indole-3-acetamide (from step (a), 19.85 g, 67.3 mmol) in tetrahydrofuran (100 ml) was added dropwise to a slurry of lithium aluminium hydride (7.66 g, 0.2 mol) in tetrahydrofuran (20 ml) under a nitrogen atmosphere, maintaining the temperature below 5° C. The yellow green slurry was then warmed to ambient temperature and then brought to gentle reflux. Reflux was maintained for 5 hr after which time the reaction mixture was cooled to 0° C. and isopropyl alcohol (150 ml) and IMS (150 ml) were added sequentially. The grey slurry was then warmed to ambient temperature, before 1N NaOH (100 ml) was added. The reaction mixture was then filtered through a celite (trade mark) pad and the pad washed consecutively with demineralised water (100 ml) and IMS (100 ml). The filtrate was then concentrated under reduced pressure until all alcohol had been removed and then the aqueous residue was extracted with ethyl acetate (2×200 ml). The combined organic extracts were then evaporated in vacuo to give a brown oil. This was triturated with a mixture of hexane and ethyl acetate (1:1) (30 ml) to give the subtitle compound (13.4 g, 75%) as a cream solid. m.p. 82-85° C.

Workup

  1. temperaturemaintaining the temperature below 5° C
  2. temperatureReflux
  3. temperaturewas maintained for 5 hr after which time the reaction mixture
  4. temperaturewas cooled to 0° C.
  5. additionwas added
  6. filtrationThe reaction mixture was then filtered through a celite (trade mark) pad
  7. washthe pad washed consecutively with demineralised water (100 ml) and IMS (100 ml)
  8. concentrationThe filtrate was then concentrated under reduced pressure until all alcohol
  9. customhad been removed
  10. extractionthe aqueous residue was extracted with ethyl acetate (2×200 ml)
  11. customThe combined organic extracts were then evaporated in vacuo
  12. customto give a brown oil
  13. customThis was triturated with a mixture of hexane and ethyl acetate (1:1) (30 ml)

Sources & evidence

ORD record
ord-63b6ea76dbf04f65ad1a7fd042f19046
Source dataset
uspto-grants-2001_08
Patent number
US06281357B1

Reaction notes

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