Methyl 4-chloroformylbutyrate → N-cyclohexylmethyl-N-(4-methoxycarbonylbutyryl)-tryptamine

HRID 903591Notes

Reaction equation

HRID 903591 reaction equation
[CH:1]1([CH2:7][NH:8][CH2:9][CH2:10][C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:20][O:21][C:22]([CH2:24][CH2:25][CH2:26][C:27](Cl)=[O:28])=[O:23]>>[CH:1]1([CH2:7][N:8]([C:27](=[O:28])[CH2:26][CH2:25][CH2:24][C:22]([O:21][CH3:20])=[O:23])[CH2:9][CH2:10][C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 73916Methyl 4-chloroformylbutyrateHCID 17158300N-(cyclohexylmethyl)-2-(1H-indol-3-yl)ethanamine

Product 1

HCID 23336454N-cyclohexylmethyl-N-(4-methoxycarbonylbutyryl)-tryptamineYield 84.9%

Procedure

12.0 g of N-cyclohexylmethyl-tryptamine and 8.47 g of 4-methoxycarbonylbutyryl chloride were treated in the same manner as described in Example 1. 15.2 g of N-cyclohexylmethyl-N-(4-methoxycarbonylbutyryl)-tryptamine (i.e., 3-[2-(N-cyclohexylmethyl-4-methoxycarbonylbutanamido)-ethyl]-indole) were thereby obtained. Yield: 84.9%

Sources & evidence

ORD record
ord-531fa71487414d9b928547863cf1875d
Source dataset
uspto-grants-1980_10
Patent number
US04228168

Reaction notes

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