Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Reexamination Certificate
2007-05-22
2007-05-22
Davis, Brian (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
C564S487000, C548S264800
Reexamination Certificate
active
10523734
ABSTRACT:
Process for the preparation of primary amines of formula (I):where R3 represents an alkyl, cycloalkyl or aralkyl group, by reaction of a triazolium salt of formula (II):where R1 and R2 represent hydrogen or an alkyl, aralkyl or aryl group, R4 represents an alkyl or aralkyl group or a residue of an organic polymer functionalized by an alkylating group, and A−represents a halogen, alkylsulphonate, arylsulphonate, alkyl sulphate, hydrogensulphate, hemisulphate, perchlorate or hydroxide, with a hydride, in order to obtain an amine of formula (I), which is isolated, if desired, and intermediates.
REFERENCES:
The Merck Index 12thedition (1996) , BUDAVARI ed., Merck & Co., Inc., Whitehouse Station, NJ, p. 1029, entry No. 6095.
PCT ISR for PCT/IP03/03398, Nov. 26, 2003.
Katritzky et al., “Synthesis & Highly Diastereoselective Alkylation of Chiral N- [(s,s)-3,5-Bis(1-methoxyethyl)-1,2,4-triazol-4-yl] arylimines” Tetrahedron: Assymetry, vol. 7, No. 6, pp. 1621-1630 (1996).
Enders et al., “Enantioselektive Syntheses von a-substituierten primaren Aminen durch nucleophile addition an SAMP-Hydrazone von Aldehyden,” Agnew. Chem. 98, pp. 1118-1119 (1986).
Database Crossfire Beilstein Online. Beilstein Institut zur Forderung der Chemischen Wissenschaften, Frankfurt AM Main, DE XP002239352 (1988).
Pragst et al, “Investigations about the cleavage of some pyridinium & Triazolium Ions” J. Prakt. Chem. vol. 329, No. 6 pp. 1076-1086, XP0001091247 (1987).
Enders, “Alkylation of Chiral Hydrazones,” Assymmetric Synthesis vol. 3, Academic Press Inc, pp. 275-338 (1984).
Pinner, “Ueber die Einwirkung von Hydrazin auf Imidoather,” Chem Ber. pp. 984-1009 (1894).
Advanced Organic Chemistry, Reactions, Mechanisms and Structure, John Wiley & Sons, 4thed. 6-35 pp. 934-935 (1992).
Advanced Organic Chemstry, Reactions,, Mechanisms, Structure; John Wiley & Sons 6-26, p. 918 (1992).
Advanced Organic Chemistry, Reactions, Mechanisms Structure; John Wiley & Sons 9-51, p. 1219 (1992.
Martinez-Diaz et al., “Preparation & Enantiomeric Purity Determination of New Chiral C2 Building Blocks Based on the 4-Amino-1,2,4-triazole Unit,” Tetrahedron: Assymetry vol. 5. No. 7 pp. 1291-1296 (1994).
Matsuda et al, “Reaction of 4-Amino-1,2,4-Triazolium Salts w/ Polarized Olefins,” Heterocycles, vol. 41, No. 12, pp. 2777-2784 (1995).
Alonzo et al., “Proton-Ionizable Macrocycles Containing 1,2,4-Triazole and 4-amino-1,2,4-triazole Subunits,” Heterocycles, vol. 26, No. 4, pp. 989-1000 (1987).
Glover et al., “Sythesis of 1,1′-Dimethyl-4,4′-azo-1,2,4-triazolium and 3,3′-Dimethtyl-1,1′-azobenzotriazolium Salts,” J. Chem. Soc. Perkins Trans. 1 pp. 1792-1794 (1974).
Becker et al.., “Azocoupling of Quaternary 1,2,4-Triazolium Salts to form 5-p-N,N-Dimethylaminophenylazo-1,2,4-triazolium Salts,” Journal fur Praktische Chemie 330 pp. 325-337 (1988).
Alcalde et al., “Non-classical [14] Metaheterophanes Containing Betaine Units. Synthesis NMR Spectroscopy & X-Ray Crystallography,” J. Chem. Soc., Chem. Commun pp. 1239-1240 (1995).
PCT International Preliminary Examination Report for PCT/IB03/03398, Jul. 19, 2004.
PCT Written Opinion for PCT/IB03/03398, mailed Mar. 23, 2004.
Roussel Christian
Serradeil Albalat Muriel
Vallejos Jean-Claude
Wilhelm Didier
Bisulca Anthony A.
Clariant (France)
Davis Brian
LandOfFree
Process for the preparation of primary amines does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Process for the preparation of primary amines, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for the preparation of primary amines will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3741800