Indole → Bromopropylphthalimide
Reaction equation
N1C2C(=CC=CC=2)C=C1.NCCC1C2C(=CC=CC=2)NC=1.CC(NCCC1C2C=C(OC)C=CC=2NC=1)=O.[C:39]1(=[O:49])[NH:43][C:42](=[O:44])[C:41]2=[CH:45][CH:46]=[CH:47][CH:48]=[C:40]12.[K].[Br:51][CH2:52][CH2:53][CH2:54]Br>>[Br:51][CH2:52][CH2:53][CH2:54][C:48]1[CH:47]=[CH:46][CH:45]=[C:41]2[C:42]([NH:43][C:39](=[O:49])[C:40]=12)=[O:44]Participants
Procedure
A method of synthesizing an indole derivative of the tryptamine type particularly melatonine, comprising the steps of 1) reacting potassium phthalimide and 1,3-di-bromopropane to obtain 3-bromopropylphthalimide; 2) reacting 3-bromopropylphthalimide with sodium acetoacetic ester in ethanol to obtain ethyl-2-acetyl-5-phthalimidopentanoate; 3) reacting the product from step 2) with diazo-p-anisidine to obtain 2-carboxyethyl-3-(2-phthalimidoethyl)-5-methoxy-indole; 4) reacting the 2-carboxyethyl-3-(2-phthalimidoethyl)-5-methoxy-indole with 2N/NaOH and then 20% H2SO4 to obtain impure 5-methoxytriptamine, which is purified by means of hexamethyldisilazane. The mono and disubstituted derivatives are obtained and the monosubstituted derivative is hydrolyzed with aqueous methanol and then recrystallized from ethanol. The N-acetyl derivative is prepared by reaction with acetic anhydride. Melatonine of high purity is obtained for prophylaxy and also against AIDS (Acquired Immuno Deficiency Syndrome).
Sources & evidence
- ORD record
- ord-853ef2ff94ed4f2e8151f71e254e34b8
- Source dataset
- uspto-grants-1992_06
- Patent number
- US05122535
Reaction notes
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