5-Methoxytryptamine → 9-Methoxy-2,3,4,6,7,12-hexahydroindolo[2,3-a]quinolizin-4-one

HRID 1004052Notes

Reaction equation

HRID 1004052 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](OCC)(=O)[CH2:16][CH2:17][CH2:18][C:19](OCC)=[O:20]>CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:14]=[C:13]2[C:9]3[CH2:10][CH2:11][N:12]4[C:15]([C:8]=3[NH:7][C:6]2=[CH:5][CH:4]=1)=[CH:16][CH2:17][CH2:18][C:19]4=[O:20]

Participants

4

Reactant 2

HCID 18335-MethoxytryptamineHCID 13163Diethyl glutarate

Product 1

HCID 187942129-Methoxy-2,3,4,6,7,12-hexahydroindolo[2,3-a]quinolizin-4-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-methoxytryptamine (420 mg) and diethyl glutarate (460 mg) is heated at 175° C. for 18 h. eparation on a column (eluent: EtOAc) gives the amide ster 2. This product is treated with a trace of ara-toluenesulphonic acid in xylene and the water formed is removed using Dean-Stark apparatus. After refluxing for 9 h and separation on a silica plate, N-[2-(5-methoxy)indol-3-ylethyl)]glutarimide is obtained.

Sources & evidence

ORD record
ord-fef6b6529bbb4929a6e7031e4277a965
Source dataset
uspto-grants-2000_04
Patent number
US06048868

Reaction notes

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