HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ammonium Hydroxide → Chloromethyl tetrahydro-beta-carboline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ammonium Hydroxide | HCID 14923 | — |
| Reactant | Tryptamine hydrochloride | HCID 67652 | — |
| Reactant | Methyl 3-chloro-2-oxopropanoate | HCID 12530121 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | Chloromethyl tetrahydro-beta-carboline | HCID 20472064 | 77.4% |
Reaction Steps
A suspension of 108.4 g (0.55 mol) of tryptaminehydrochloride in 1 liter of dry methanol and 93.2 g (0.68 mol) of methyl-3-chloropyruvate* was refluxed under N2 for 24 h. The cooled mixture was poured into brine, made basic with ammonium hydroxide and extracted with dichloromethane. Concentration and trituration with ethyl acetate gave 94.0 g (61.3%) of the chloromethyl tetrahydro-β-carboline, melting point ("mp") 123°-125° C. The product was recrystallized from dichloromethane/pentane.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04362739 |
| Source dataset | uspto-grants-1982_12 |
| ORD ID | ord-aca795ff1c6743918c9c5449702998c6 |
| Source note | uspto-grants-1982_12 |