Methyltryptamine → N-methyl-N-(4-methoxycarbonylbutyryl)-tryptamine

HRID 903586

Reaction equation

[CH3:1][NH: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.[CH3:14][O:15][C:16]([CH2:18][CH2:19][CH2:20][C:21](Cl)=[O:22])=[O:17]>>[CH3:1][N:2]([C:21](=[O:22])[CH2:20][CH2:19][CH2:18][C:16]([O:15][CH3:14])=[O:17])[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

Participants

Reactant 2

HCID 6088Methyltryptamine

HCID 73916Methyl 4-chloroformylbutyrate

Product 1

HCID 23336480N-methyl-N-(4-methoxycarbonylbutyryl)-tryptamineYield 92.9%

Procedure

10.3 g of N-methyl-tryptamine (i.e., 3-(2-methylaminoethyl)-indole) and 11.7 g of 4-methoxycarbonylbutyryl chloride were treated in the same manner as described in Example 1. 16.6 g of N-methyl-N-(4-methoxycarbonylbutyryl)-tryptamine (i.e., 3-[2-(N-methyl-4-methoxycarbonylbutanamido)ethyl]indole) were therby obtained. Yield: 92.8%

Sources & evidence

ORD record: ord-a29b862b14cd4be6ab465ec07efaf95d
Source dataset: uspto-grants-1980_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04228168

Linked notes

Loading…