Tryptamine → HCID 15083993, compound

HRID 267553

Reaction equation

HRID 267553 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:13](O)(=[O:19])[CH2:14][CH2:15][C:16]([CH3:18])=O>CCCCOCCO>[CH3:18][C:16]12[C:5]3[NH:6][C:7]4[C:12]([C:4]=3[CH2:3][CH2:2][N:1]1[C:13](=[O:19])[CH2:14][CH2:15]2)=[CH:11][CH:10]=[CH:9][CH:8]=4

Participants

4

Reactant 2

HCID 1150TryptamineHCID 11579Levulinic Acid

Product 1

HCID 15083993HCID 15083993, compound

Reagents, catalysts & solvents 1

HCID 81332-ButoxyethanolSolvent

Procedure

Tryptamine (112.15 g.), levulinic acid (97.6 g., 85.6 ml.) and butyl cellosolve (1 liter) are refluxed under nitrogen for 16 hours and the solvent is removed. The residue is successively washed with water, dilute aqueous sodium hydroxide, water, dilute aqueous hydrochloric acid, water and dried. Trituration of the crude product, decomposition at 252°-262°C., with methanol, and then with benzene, and drying provides 120.4 g. of the title compound, decomposition at 259°-263°C.; λmaxKBr 3.09, 6.01, 6.17, 13.38 μ.

Workup

  1. customthe solvent is removed
  2. washThe residue is successively washed with water, dilute aqueous sodium hydroxide, water, dilute aqueous hydrochloric acid, water
  3. customdried
  4. dry with materialTrituration of the crude product, decomposition at 252°-262°C., with methanol, and then with benzene, and drying
  5. customprovides 120.4 g

Sources & evidence

ORD record
ord-57fe05309dae4472a9ac00f0582f7e80
Source dataset
uspto-grants-1976_03
Patent number
US03943148

Linked notes

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