Ammonia → 3-Acetyl-1-(2-chlorobenzyl)-2-propylindole-6-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Ammonia	HCID 222	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	3-Acetyl-1-(2-chlorobenzyl)-2-propylindole-6-carboxylic acid	HCID 9820688	—
Solvent	Methanol	HCID 887	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	3-Acetyl-1-(2-chlorobenzyl)-2-propylindole-6-carboxamide	HCID 10155921	90.8%

Reaction Conditions

Temperature	2 °C

Reaction Steps

To a solution of 3-acetyl-1-(2-chlorobenzyl)-2-propylindole-6-carboxylic acid (74 mg) in dimethylformamide (2 ml) were added 1-hydroxybenzotriazole (38 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (98 mg) and 3N methanol solution of ammonia (0.5 ml). After stirred at 2° C. for 14 hours, the resulting mixture was diluted with ethyl acetate. The organic phase was washed successively with 1N hydrochloric acid, water, aqueous sodium bicarbonate and brine, dried over sodium sulfate and evaporated in vacuo. The residue was triturated with isopropyl ether to give 3-acetyl-1-(2-chlorobenzyl)-2-propylindole-6-carboxamide (67 mg) as colorless crystals.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06069156
Source dataset	uspto-grants-2000_05
ORD ID	ord-57ef45dcc37b4e04b55214d198126fe0
Source note	uspto-grants-2000_05