5-Methoxytryptamine → Melatonin

HRID 893082Notes

Reaction equation

HRID 893082 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[C:13]2[C:6]([NH:7][CH:8]=[C:9]2[CH2:10][CH2:11][NH2:12])=[CH:5][CH:4]=1.[C:15](OC(=O)C)(=[O:17])[CH3:16]>C(Cl)Cl>[CH3:16][C:15]([NH:12][CH2:11][CH2:10][C:9]1[C:13]2[CH:14]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=2[NH:7][CH:8]=1)=[O:17]

Participants

4

Reactant 2

HCID 18335-MethoxytryptamineHCID 7918Acetic Anhydride

Product 1

HCID 896MelatoninYield 0.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension, cooled in ice, of 5 g (26.3 moles) of 5-methoxytryptamine (in a raw condition) in 100 ml methylene chloride there is slowly added, under stirring, a cold solution of 5 ml (52.6 moles) of acetic anhydride in 50 ml of methylene chloride. Stirring and cooling are continued for 1 hour (the reaction progression can be controlled by TLC), so as to obtain a full solution; then the solution is washed by Na2CO3 2N×2, under strong stirring, and then by water. The organic phase, dried on anhydrous Na2SO4 and evaporated, provides 6 g of raw melatonine, which is purified by chromatography on column (4 cm; diameter/length ratio 1:5) of Merck silica gel (70-230 mesh) (120 g); the solution is eluted by methylene chloride in order to remove the scarcely polar products thereby providing pure melatonine by eluting with methylene chloride-acetone (8:2). There are obtained 4 g of product (purifying yield 65%) which are crystalized from acetone-water. Melting point 116°-7° C.

Workup

  1. additionthere is slowly added
  2. stirringStirring
  3. temperaturecooling
  4. customto obtain a full solution
  5. washthen the solution is washed by Na2CO3 2N×2, under strong stirring
  6. dry with materialThe organic phase, dried on anhydrous Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-8cc6cfb898114adaba469745e3770411
Source dataset
uspto-grants-1992_06
Patent number
US05122535

Reaction notes

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