5-Methoxytryptamine → Melatonin

HRID 893081Notes

Reaction equation

HRID 893081 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 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension, cooled in ice, of 20 g (0.105 moles) of pure 5-methoxytryptamine in 400 ml methylene chloride there is slowly added, under stirring, a cold solution of 20 ml (0.21 moles) of acetic anhydride in 200 ml methylene chloride. Stirring and cooling are continued for 1 hour (the reaction progression can be controlled by TCL) so as to obtain a full solution; then the solution is washed with Na2CO3 ×2, under long stirring, and then with water. The organic phase, dried on Na2SO4 and evaporated, provides 24 g (yield 98%) of lightly colored melatonine.

Workup

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

Sources & evidence

ORD record
ord-d7456fbea0ec409fafa219a638cdc793
Source dataset
uspto-grants-1992_06
Patent number
US05122535

Reaction notes

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