1978
DOI: 10.1135/cccc19781760
|View full text |Cite
|
Sign up to set email alerts
|

4,4-Bis(4-fluorophenyl)butylamines and their cyclic analogues; An efficient synthesis of the neuroleptic penfluridol

Abstract: Modification of the reaction of 4-(4-fluorophenyllbutyrc1actone with fiucrobenzene and aluminium chloride led to a reliable synthesis of 4,4-bis(4-fiucrophenyl)butyric acid (II). Its reduction with sodium dihydridobis(2-methoxyethoxy)aluminate afforded the alcohcl III giving by treatment with hydrobromic acid the bromide IV. The alkylation of 4-(4-chloro-3-trifiuoromethylphenyl)-4-piperidinol with bromide IV represents the last step of an efficient synthesis of the neuroleptic agent penfiuridol (I). Alkylation… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
2
2
1

Citation Types

0
18
0

Year Published

1978
1978
2018
2018

Publication Types

Select...
4
1
1

Relationship

0
6

Authors

Journals

citations
Cited by 10 publications
(18 citation statements)
references
References 4 publications
0
18
0
Order By: Relevance
“…For the bromo compounds 2c-e, we found Department of Chemistry, University College London, 20 Gordon Street, London, U.K. WC1H 0AJ. E-mail: f.d.king@ucl.ac.uk, a.e.aliev@ucl.ac.uk † Electronic supplementary information (ESI) available: 1 H NMR and 13 C NMR for all compounds. CCDC reference numbers 787503.…”
Section: Resultsmentioning
confidence: 99%
See 4 more Smart Citations
“…For the bromo compounds 2c-e, we found Department of Chemistry, University College London, 20 Gordon Street, London, U.K. WC1H 0AJ. E-mail: f.d.king@ucl.ac.uk, a.e.aliev@ucl.ac.uk † Electronic supplementary information (ESI) available: 1 H NMR and 13 C NMR for all compounds. CCDC reference numbers 787503.…”
Section: Resultsmentioning
confidence: 99%
“…This cyclisation works well for mildly deactivated phenyls, such as the dibromo 2f but not for the strongly deactivated nitro 2j. At room temperature, the NMR spectra of the pyrrolobenazocinones were often poorly resolved, with peak broadening, and peaks were often missing in the 13 C spectrum.…”
Section: Resultsmentioning
confidence: 99%
See 3 more Smart Citations