Georg Thieme Verlag KG
Synthesis
,  volume 44 ,  issue 14 ,  pages 2231-2236

A Practical Synthesis of 2-{4-[4-Fluoro-3-(trifluoromethyl)phenyl]-2-(piperidin-4-yl)-1H-imidazol-1-yl}-N,N-dimethylethanamine

Radhe Vaid 1
, 
Jeremy Spitler 1
, 
Sathish Boini 1
, 
Kenneth Henry 2
, 
Jiansheng Xu 3
, 
Baitao Gao 3
, 
Xiaoquan Lu 3
1
 
Chemical Product Research and Development, A Division of Eli Lilly and Company
2
 
Discovery Chemistry Research and Technologies, A Division of Eli Lilly and Company
3
 
Shanghai PharmaExplorer | 
Publication type: Journal Article
Publication date: 2012-06-13
Georg Thieme Verlag KG
scimago Q2
wos Q2
SJR: 0.559
CiteScore: 4.6
Impact factor: 2.3
ISSN: 00397881, 1437210X
Catalysis
Organic Chemistry
Abstract
A practical synthesis of the title compound was accomplished by hydrogenation of 2-{4-[4-fluoro-3-(trifluoromethyl)phenyl]-2-(pyridin-4-yl)-1 H -imidazol-1-yl}- N , N -dimethylethanamine. The latter was obtained by N-alkylation of 4-{4-[4-fluoro-3-(trifluoromethyl)phenyl]-1 H -imidazol-2-yl}pyridine. Treatment of N -{2-[4-fluoro-3-(trifluoromethyl)phenyl]-2-oxoethyl}isonicotinamide hydrochloride with ammonium acetate in acetic acid provided 4-{4-[4-fluoro-3-(trifluoromethyl)phenyl]-1 H -imidazol-2-yl}pyridine. Coupling of 2-amino-1-[4-fluoro-3-(trifluoromethyl)phenyl]ethanone 4-methylbenzene sulfonate with pyridine 4-carboxylic acid using either T 3 P or EDCI-HOBt provided N -{2-[4-fluoro-3-(trifluo­romethyl)phenyl]-2-oxoethyl}isonicotinamide hydrochloride.
Found 
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GOST |
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GOST Copy
Vaid R. et al. A Practical Synthesis of 2-{4-[4-Fluoro-3-(trifluoromethyl)phenyl]-2-(piperidin-4-yl)-1H-imidazol-1-yl}-N,N-dimethylethanamine // Synthesis. 2012. Vol. 44. No. 14. pp. 2231-2236.
GOST all authors (up to 50) Copy
Vaid R., Spitler J., Boini S., Henry K., Jiansheng Xu, Gao B., Lu X. A Practical Synthesis of 2-{4-[4-Fluoro-3-(trifluoromethyl)phenyl]-2-(piperidin-4-yl)-1H-imidazol-1-yl}-N,N-dimethylethanamine // Synthesis. 2012. Vol. 44. No. 14. pp. 2231-2236.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1055/s-0031-1290371
UR - https://doi.org/10.1055/s-0031-1290371
TI - A Practical Synthesis of 2-{4-[4-Fluoro-3-(trifluoromethyl)phenyl]-2-(piperidin-4-yl)-1H-imidazol-1-yl}-N,N-dimethylethanamine
T2 - Synthesis
AU - Vaid, Radhe
AU - Spitler, Jeremy
AU - Boini, Sathish
AU - Henry, Kenneth
AU - Jiansheng Xu
AU - Gao, Baitao
AU - Lu, Xiaoquan
PY - 2012
DA - 2012/06/13
PB - Georg Thieme Verlag KG
SP - 2231-2236
IS - 14
VL - 44
SN - 0039-7881
SN - 1437-210X
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2012_Vaid,
author = {Radhe Vaid and Jeremy Spitler and Sathish Boini and Kenneth Henry and Jiansheng Xu and Baitao Gao and Xiaoquan Lu},
title = {A Practical Synthesis of 2-{4-[4-Fluoro-3-(trifluoromethyl)phenyl]-2-(piperidin-4-yl)-1H-imidazol-1-yl}-N,N-dimethylethanamine},
journal = {Synthesis},
year = {2012},
volume = {44},
publisher = {Georg Thieme Verlag KG},
month = {jun},
url = {https://doi.org/10.1055/s-0031-1290371},
number = {14},
pages = {2231--2236},
doi = {10.1055/s-0031-1290371}
}
MLA
Cite this
MLA Copy
Vaid, Radhe, et al. “A Practical Synthesis of 2-{4-[4-Fluoro-3-(trifluoromethyl)phenyl]-2-(piperidin-4-yl)-1H-imidazol-1-yl}-N,N-dimethylethanamine.” Synthesis, vol. 44, no. 14, Jun. 2012, pp. 2231-2236. https://doi.org/10.1055/s-0031-1290371.