Ammonium Hydroxide → Chloromethyl tetrahydro-beta-carboline

HRID 1902254Notes

Reaction equation

HRID 1902254 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1.COC(=O)[C:17]([CH2:19][Cl:20])=O.[OH-].[NH4+]>CO.[Cl-].[Na+].O>[Cl:20][CH2:19][CH:17]1[C:6]2[NH:7][C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:5]=2[CH2:4][CH2:3][NH:2]1

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 67652Tryptamine hydrochlorideHCID 12530121Methyl 3-chloro-2-oxopropanoate

Product 1

HCID 20472064Chloromethyl tetrahydro-beta-carbolineYield 77.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

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.

Workup

  1. temperaturewas refluxed under N2 for 24 h
  2. extractionextracted with dichloromethane
  3. concentrationConcentration and trituration with ethyl acetate

Sources & evidence

ORD record
ord-aca795ff1c6743918c9c5449702998c6
Source dataset
uspto-grants-1982_12
Patent number
US04362739

Reaction notes

Loading…