HCID 13236295, compound → N,N-Dimethyltryptamine

HRID 1156579Notes

Reaction equation

HRID 1156579 reaction equation
[CH3:1][N:2]([CH3:23])[C:3](=O)[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]=1C1C(CC)=NOC=1C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:1][N:2]([CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)[CH3:23]

Participants

4

Reactant 2

HCID 13236295HCID 13236295, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 6089N,N-Dimethyltryptamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4.7 g. (0.015 mole) of N,N-dimethyl-2-(3-ethyl-5-methyl-4-isoxazolyl)-3-indoleacetamide in 47 ml. of tetrahydrofuran under nitrogen is added dropwise to a suspension of 2.28 g. (0.06 mole) lithium aluminum hydride in 50 ml. tetrahydrofuran, while maintaining the reaction at room temperature. The mixture is stirred for 11/2 hours at room temperature, cooled in ice and quenched with 5 ml. water in 50 ml. tetrahydrofuran. The resulting solids are filtered and the filtrate dried over anhydrous magnesium sulfate, filtered and evaporated and the residue crystallized from ether to give 2-(3-ethyl-5-methyl)-4-isoxazolyl)-3-(dimethylaminoethyl)-indole; m.p. 118° to 120° C.

Workup

  1. customthe reaction at room temperature
  2. temperaturecooled in ice
  3. customquenched with 5 ml
  4. filtrationThe resulting solids are filtered
  5. dry with materialthe filtrate dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customthe residue crystallized from ether

Sources & evidence

ORD record
ord-cdc49048299545cabe94936fc3bf3994
Source dataset
uspto-grants-1982_06
Patent number
US04336378

Reaction notes

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