O-Methylbufotenine → HCID 11806221, compound

HRID 635387Notes

Reaction equation

HRID 635387 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[C:15]2[C:6]([NH:7][CH:8]=[C:9]2[CH2:10][CH2:11][N:12]([CH3:14])[CH3:13])=[CH:5][CH:4]=1>[Pd].Cl>[CH3:13][N:12]([CH2:11][CH2:10][CH:9]1[C:15]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:16]=2)[NH:7][CH2:8]1)[CH3:14]

Participants

4

Reactant 1

HCID 1832O-Methylbufotenine

Product 1

HCID 11806221HCID 11806221, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 5-methoxy-N,N-dimethyltryptamine (0.200 g, 0.939 mmol) and palladium on carbon (10%, 200 mg) in 50 M aqueous HCl (50 ml) was hydrogenated at 50 psi overnight. The catalyst was removed by filtration, and the filtrate was extracted with dichloromethane (3×25 ml). The combined organic extracts were evaporated in vacuo and the residue was purified by flash chromatography (silica gel, CH2Cl2—MeOH—NH3(aq); 92:8:0.8) to give 94 mg (47%) of the title compound; δH (250 MHz, CDCl3) 1.71 (1H, m), 1.99 (1H, m), 2.26 (6H, s), 2.37 (2H, m), 3.20 (1H, t, J=8.0 Hz), 3.27 (1H, m), 3.68 (1H, t, J=8.0 Hz), 3.75 (3H, s), 6.60-6.61 (2H, m), 6.73 (1H, m).

Workup

  1. customwas hydrogenated at 50 psi overnight
  2. customThe catalyst was removed by filtration
  3. extractionthe filtrate was extracted with dichloromethane (3×25 ml)
  4. customThe combined organic extracts were evaporated in vacuo
  5. customthe residue was purified by flash chromatography (silica gel, CH2Cl2—MeOH—NH3(aq); 92:8:0.8)

Sources & evidence

ORD record
ord-1f06d192eec84c629310671764f96409
Source dataset
uspto-grants-2001_02
Patent number
US06187805B1

Reaction notes

Loading…