Tryptamine → N-(p-Methoxybenzyloxycarbonyl)tryptamine

HRID 1079373Notes

Reaction equation

HRID 1079373 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.C(N(CC)CC)C.[CH3:20][O:21][C:22]1[CH:42]=[CH:41][C:25]([CH2:26][O:27][C:28](ON=C(C2C=CC=CC=2)C#N)=[O:29])=[CH:24][CH:23]=1>O.O1CCOCC1.[Cl-].[Na+]>[CH3:20][O:21][C:22]1[CH:42]=[CH:41][C:25]([CH2:26][O:27][C:28]([NH:1][CH2:2][CH2:3][C:4]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][CH:5]=2)=[O:29])=[CH:24][CH:23]=1

Participants

7

Reactant 3

HCID 1150TryptamineHCID 8471TriethylamineHCID 39162272-(4-Methoxybenzyloxycarbonyloxyimino)-2-phenylacetonitrile

Product 1

HCID 15379889N-(p-Methoxybenzyloxycarbonyl)tryptamineYield 81%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 5234Sodium ChlorideSolventHCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 0.70 g (4.7 mmol) of tryptamine in 2.5 mL of deionized water and 0.65 mL (4.7 mmol) of triethylamine in a round bottom flask, equipped with an argon inlet, was added 1.45 g (4.7 mmol) of 2-(4-methoxybenzyloxycarbonyloxyimino)-2-phenylacetonitrile (MoZ-ON, Aldrich) in 5 mL of dioxane. During the first 5-10 minutes of stirring, the mixture became clear. This mixture was stirred for an additional 6 hours and diluted with 150 mL of saturated sodium chloride solution and extracted with 2×50 mL of ethyl acetate. The organic extracts were dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography using hexane:ethyl acetate (1:1) as an eluent to yield (81%) N-(p-Methoxybenzyloxycarbonyl)tryptamine as white solid, mp. 108°-109° C.

Workup

  1. customequipped with an argon inlet
  2. stirringThis mixture was stirred for an additional 6 hours
  3. extractionextracted with 2×50 mL of ethyl acetate
  4. dry with materialThe organic extracts were dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-287b863aab6043a990544c29003fc0dd
Source dataset
uspto-grants-1996_12
Patent number
US05580878

Reaction notes

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