Tryptamine → N-Acetyltryptamine

HRID 1095501

Reaction equation

HRID 1095501 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.[C:20](OC(=O)C)(=[O:22])[CH3:21]>C1COCC1>[NH:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4]([CH2:3][CH2:2][NH:1][C:20](=[O:22])[CH3:21])=[CH:5]1

Participants

5

Reactant 3

HCID 1150TryptamineHCID 7918Acetic AnhydrideHCID 8471Triethylamine

Product 1

HCID 70547N-Acetyltryptamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tryptamine (192 mg/1.2 mmol) was initially introduced into abs. THF (5 ml), and triethylamine (179 μl/1.3 mmol) was added. Acetic anhydride (132 mg/1.3 mmol) was then added and the mixture was stirred at RT for 4 h. The mixture was concentrated to dryness i. vac. The residue was taken up in ethyl acetate and this solution was washed with saturated NaHCO3 solution (two times 20 ml) and with NaCl solution (two times 20 ml). The organic phase was dried over Na2SO4 and concentrated i. vac.

Workup

  1. concentrationThe mixture was concentrated to dryness i
  2. washthis solution was washed with saturated NaHCO3 solution (two times 20 ml) and with NaCl solution (two times 20 ml)
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated i

Sources & evidence

ORD record
ord-2ce0a80823754975b947e0a7fceb9774
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Linked notes

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