3478-91-9

Usage

Uses

Used in Pharmaceutical Development:
N,N-dimethyl-2-(2-nitrophenyl)ethanamine is used as a pharmaceutical intermediate for the development of drugs targeting the central nervous system. Its psychoactive and stimulant effects make it a candidate for potential therapeutic applications, such as in the treatment of certain neurological or psychiatric disorders.
Used in Research:
In the scientific community, N,N-dimethyl-2-(2-nitrophenyl)ethanamine is utilized as a research compound to study the effects of psychoactive substances on the central nervous system. This helps in understanding the mechanisms of action and potential therapeutic uses, as well as the risks associated with its psychoactive properties.
Used in Controlled Substances Regulation:
Due to its psychoactive and stimulant effects, N,N-dimethyl-2-(2-nitrophenyl)ethanamine is used in the context of controlled substances regulation to ensure that its production, distribution, and use are monitored and controlled to prevent misuse and abuse.

Synthetic route

(2-nitrobenzyl)dimethyl<(trimethylsilyl)methyl>ammonium bromide → dimethyl-(2-nitro-phenethyl)-amine (3478-91-9)

Conditions	Yield
With cesium fluoride In N,N,N,N,N,N-hexamethylphosphoric triamide for 24h; Ambient temperature; Yield given;

(2-bromoethyl)-2-nitrobenzene (16793-89-8) + dimethyl amine (124-40-3) → dimethyl-(2-nitro-phenethyl)-amine (3478-91-9)

Conditions	Yield
In ethanol

formaldehyd (50-00-0) + 2-nitro-β-phenethylamine hydrochloride → dimethyl-(2-nitro-phenethyl)-amine (3478-91-9)

Conditions	Yield
at 135℃;

bromhydric acid + 2-nitro-benzeneethanol (15121-84-3) → dimethyl-(2-nitro-phenethyl)-amine (3478-91-9)

Conditions	Yield
With dimethyl amine In ethanol

dimethyl-(2-nitro-phenethyl)-amine (3478-91-9) → (2-amino-phenethyl)-dimethyl-amine (3478-92-0)

Conditions	Yield
aluminum nickel In methanol	89%
(catalytic hydrogenation);

dimethyl-(2-nitro-phenethyl)-amine (3478-91-9) + 1-methoxy-2,4,6-trinitrobenzene (606-35-9) → trimethyl-(2-nitro-phenethyl)-ammonium; picrate

Conditions	Yield
With benzene

dimethyl-(2-nitro-phenethyl)-amine (3478-91-9) → N-Cinnamoyl-2-<2-dimethylamino-ethyl>-anilin (3478-82-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: (catalytic hydrogenation) 2: CHCl3 View Scheme

Upstream product

• 15121-84-3 2-nitro-benzeneethanol 
• 50-00-0 formaldehyd 
• 16793-89-8 (2-bromoethyl)-2-nitrobenzene 
• 124-40-3 dimethyl amine 

Downstream Products

• 3478-82-8 N-Cinnamoyl-2-<2-dimethylamino-ethyl>-anilin 
• 3478-92-0 (2-amino-phenethyl)-dimethyl-amine 

Relevant academic research and scientific papers

Rearrangement of (Substituted benzyl)trimethylammonium Ylides in a Nonbasic Medium: The Improved Sommelet-Hauser Rearrangement

Benzyl quaternary ammonium ylide formation in a nonbasic medium was accomplished by fluoride anion induced desilylation of benzyldimethylammonium bromide (3a) and ortho- or para-substituted benzyl analogues 3b-k.Treatment of 3 with CsF in HMPA at room temperature gives high yields of the Sommelet-Hauser rearrangement products 7 from 3a and methyl-, acetoxy-, and chloro-substituted analogues 3b-f.However, formation of the Stevens rearrangement products 8 is competitive for the reaction of compounds 3g-k having strong electron-withdrawing substituents such as acetyl, cyano, and nitrogen groups.From the o-cyano-substituted analogue 3h, a considerable amount of para Sommelet-Hauser rearrangement product is isolated.

Orthoarylideneaminophenethylamines and pharmaceutical compositions

Compounds, exhibiting central nervous system activity, of the formula STR1 wherein R1 is phenyl which is unsubstituted or substituted by at least one member selected from the group consisting of halogen, CF3, C1 -C4 alkyl, C1 -C4 alkoxy and COOH, or R1 is STR2 or R1 is a heterocycle selected from the group consisting of STR3 R2 R3 R4 and R5, which may be identical or different, are H or CH3 ; R6 and R7, which may be identical or different, are C1 -C6 alkyl, which may be straight-chained or branched, or R7 can be H when R6 is a branched-chain alkyl, or R6 and R7 can form, with the nitrogen to which they are bonded, a heterocycle selected from the group consisting of STR4 R8 R9 R10 and R11, which may be identical or different, are H, halogen, CF3, hydroxy or C1 -C4 alkoxy, or two contiguous members of R8 R9, R10 and R11 may together form a chain --O--(CH2)n --O--, where n=1 or 2, or a chain --O--CH2 --O--CH2 --; and pharmaceutically acceptable addition salts thereof are disclosed, along with a method of producing the same, and pharmaceutical compositions comprising the same.