23694-03-3

Upstream product

• 26116-12-1 1-ethyl-2-pyrrolidinemethanamine 
• 90763-46-5 2-methoxy-5-nitrobenzoyl chloride 
• 40751-89-1 2-methoxy-5-nitrobenzoic acid 

Downstream Products

• 68255-81-2 N-(1-ethyl-2-pyrrolidinylmethyl)-2-methoxy-5-aminobenzamide 
• 90763-40-9 C₂₀H₃₄N₄O₄S 
• 90763-33-0 N-(1-ethyl-2-pyrrolidinylmethyl)-2-methoxy-5-t-butylaminosulfonamidobenzamide 
• 90763-43-2 C₁₆H₂₆N₄O₄S 
• 90763-34-1 N-(1-Ethyl-pyrrolidin-2-ylmethyl)-2-methoxy-5-(2,2,2-trifluoro-acetylamino)-benzamide 
• 90763-31-8 C₁₆H₂₆N₄O₄S 
• 90763-37-4 N-(1-Ethyl-pyrrolidin-2-ylmethyl)-2-methoxy-5-methylamino-benzamide 
• 68255-83-4 N-(1-ethyl-2-pyrrolidinylmethyl)-2-methoxy-5-methanesulfonamidobenzamide 
• 68256-26-8 N-(1-ethyl-2-pyrrolidinylmethyl)-2-methoxy-5-aminosulfonamidobenzamide 

Relevant academic research and scientific papers

POTENTIAL NEUROLEPTICS OF THE ORTHOPRAMIDE SERIES; SYNTHESIS OF HETEROCYCLIC 5-AMINO-2-METHOXYBENZAMIDES AND OF SOME RELATED COMPOUNDS

2-Methoxy-5-nitrobenzoyl chloride was reacted with 2-(aminoethyl)-1-ethylpyrrolidine, 3-amino-1-ethylpiperidine, 4-amino-1-benzylpiperidine, 1-benzylpiperazine, and 1-amino-4-benzylpiperazine and gave the N-substituted 2-methoxy-5-nitrobenzamides VIa-VIe.Their reduction with hydrazine hydrate and Raney nickel in ethanol afforded the corresponding 5-amino-2-methoxybenzamides VIIa-VIIe.The amino amides VIIb and VIIc were transformed to methylamino compounds XIb and XIc via the 4-toluenesulfonamides VIIIb and VIIIc and the N-methyl-4-toluenesulfonamides Xb and Xc.The N-(1-benzyl-4-piperidinyl)amides VIc, VIIc, and XIc were found to be mild neuroleptics having antiapomorphine, some cataleptic and some ataxic activity.

Synthesis and Neuroleptic Activity of N--2-methoxy-5-sulfonamidobenzamides

A series of some novel N-benzamides involving replacement of the sulfamoyl group in sulpiride with a sulfonamido group was synthesized and tested for dopamine receptor blockade.In comparison with sulpiride, several compounds were considerably more potent than sulpiride as dopamine receptor blockers.The structure-activity relationships are discussed.