Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzylamine | HCID 7504 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 7-(3-Bromopropyl)-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione | HCID 90018 | — |
| Reactant | N-Benzyl-5-benzyloxytryptamine | HCID 11727997 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Product | Tryptamine | HCID 1150 | — |
Reaction Steps
N-Benzyl-5-benzyloxytryptamine, which can be prepared by the procedure of Speeter and Anthony, J.A.C.S., 76, 6208 (1954) by reacting 5-benzyloxy-3-indol-glyoxylyl chloride with benzylamine and reducing the product with lithium aluminium hydride, is reacted with 3-(theophyllin-7-yl)propyl bromide in the presence of a weak base such as potassium carbonate to yield N-benzyl-5-benzyloxy-N-[3-theophyllin-7-yl)propyl]tryptamine. Debenzylation by hydrogenation in the presence of a platinum catalyst gives the desired compound. By starting from 5-acetoxy-3-indolglyoxylyl chloride instead of 5-benzylox-3-indol-glyoxylyl chloride and proceeding in analogous manner 5-acetoxy-N-[3-(theophyllin-7-yl)propyl]tryptamine is prepared. Treatment of this compound with ammonia solution to remove the acetyl group gives the desired compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US04406903 |
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| Source dataset | uspto-grants-1983_09 |
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| ORD ID | ord-38074a6e86874bcf96b42f267715cd61 |
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| Source note | uspto-grants-1983_09 |
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