Synthesis of N-[2-(1-piperidinyl)ethyl]benzamides

Chemical and Pharmaceutical Bulletin

Volumn 50, Issue 1, 2002, Pages 129-132

  Fujisaki, Fumiko ^a   Abe, Nobuhiro ^a   Sumoto, Kunihiro ^a  

^a FUKUOKA UNIVERSITY   (Japan)

Author keywords

piperidinoalanine; Benzamide derivative; Mannich base; Mixed anhydride; Pivaloyl chloride; Schotten Baumann reaction

Indexed keywords

ALANINE DERIVATIVE; ARGIPRESSIN[1 (3,3 CYCLOPENTAMETHYLENE 3 MERCAPTOPROPIONIC ACID) 2 (O METHYLTYROSINE)]; BENZAMIDE DERIVATIVE; BETA PIPERIDINOALANINE; KETONE; MORPHINE; N [2 (1 PIPERIDINYL)ETHYL]BENZAMIDE DERIVATIVE; UNCLASSIFIED DRUG; ALANINE; DRUG DERIVATIVE; PIPERIDINOALANINE;

ANALGESIC ACTIVITY; ARTICLE; CENTRAL NERVOUS SYSTEM; DRUG STRUCTURE; DRUG SYNTHESIS; CHEMISTRY; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

ALANINE; BENZAMIDES; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

EID: 0036370140     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.50.129     Document Type: Article

References (11)

1. For example, see Miyano S., Abe N., Takeda K., Fujisaki F., Sumoto K., Synthesis, 1982, 852 and references cited therein.
2. Prepn.: Miyano S., Abe N., Ger. Offen. 2323301 [Chem. Abstr., 80, 70539h (1974)];
3. Pharmacology: Kase Y., Saita M., Takahama K., Masaki K., Miyata T., Jpn. J. Pharmacol., 24, 85-86 (1974).
4. Abe N., Fujisaki E., Sumoto K., Chem. Pharm. Bull, 46, 142-144 (1998).
5. Compound 7 is sparingly soluble in piperidine, and the reaction did not give the desired product under the same reaction conditions. Use of additional solvent resulted in the formation of unknown polymeric products.
6. Introductions of other amino functionalities instead of a piperidine ring substituent were also successful by the procedure via a mixed anhydride. These results together with pharmacological evaluation will be described elsewhere.
7. a) Bishoff S., Bittiger H., Delini-Stula A., Ortmann R., Eur. J. Pharmacol., 79, 225-232 (1982);
8. b) Olivers J. K., Gommeron W., Leysen J. E., Jenner P., Marsden C. D., J. Pharm. Pharmacol., 40, 415-421 (1988);
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10. Dumuis A., Sebben M., Bockaert J., Naunyn-Schmideberg's Arch. Pharmacol., 340, 403-410 (1989).
11. The computational molecular model examinations were carried out by "overlay" operation combined with MM2 calculation. Some of the compounds in this series showed significant dopamine antagonist activities. These results will be described elsewhere.