78815-71-1

Basic information

• Product Name: 4-Piperidinecarboxylic acid, 1-methyl-4-(phenylmethyl)-, ethyl ester
• CAS NO: 78815-71-1
• Molecular Formula: C16H23NO2
• Molecular Weight: 261.364
• Mol File: 78815-71-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4-Piperidinecarboxylic acid, 1-methyl-4-(phenylmethyl)-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Piperidinecarboxylic acid, 1-methyl-4-(phenylmethyl)-, ethyl ester(78815-71-1)
• EPA Substance Registry System: 4-Piperidinecarboxylic acid, 1-methyl-4-(phenylmethyl)-, ethyl ester(78815-71-1)

Safety Data

• Hazardous Substances Data: 78815-71-1(Hazardous Substances Data)

Upstream product

• 24252-37-7 ethyl 1-methylisonipecotate 
• 100-39-0 benzyl bromide 
• 1623-99-0 phenyl sodium 
• 20691-92-3 1-methylpiperidine-4-carbonitrile 
• 40175-06-2 ethyl 1-methyl-1,2,5,6-tetrahydropyridine-4-carboxylate 
• 10129-59-6 1-methyl-4-ethoxycarbonylpyridinium iodide 
• 78815-69-7 6-benzyl-4-ethoxycarbonyl-1,2,3,6-tetrahydro-1-methylpyridine 
• 855638-82-3 4-benzyl-1-methyl-piperidine-4-carbonitrile 

Downstream Products

• 78815-79-9 N-methyl-1-phenylspiro-1-ol 

Relevant articles and documents

Reductive alkylation of pyridinium salts. Part 1. Synthesis of di-, tetra- and hexa-hydropyridine esters

Reaction of 1-methyl-, 1-benzyl- and 1-benzoyl-4-ethoxycarbonylpyridinium salts 1 with zinc and benzyl bromide produce regioselectively the 4,4-disubstituted 1,4-dihydropyridines 3 (R = CH3, PhCH2, PhCO); only the latter is stable but all are reduced catalytically to piperidines 2 (R = CH3, PhCH2, PhCO). 1-Benzoyl-4-ethoxycarbonylpyridinium chloride with zinc and benzoyl chloride or ethyl bromoacetate gives respectively 4-benzoyl- 18 or 4-ethoxycarbonylmethyl-1-benzoyl-4-ethoxycarbonyl-1,4-dihydropyridine 17, but 1-methyl-4-ethoxycarbonylpyridinium iodide 1 (R = CH3, X = I) with benzoyl chloride gives 3-benzoyl-4-ethoxycarbonyl-1-methyl-1,2-dihydropyridine 21.The action of zinc and benzyl bromide on 1-methyl- and 1-benzyl-3-ethoxycarbonylpyridinium salts 5 gives, after catalytic hydrogenation, mixtures of 2- and 4-benzyl-5-ethoxycarbonyl-1,2,3,4-tetrahydropyridines 6 and 7 (R = CH3 or PhCH2) but similar treatment of 1-benzoyl-3-ethoxycarbonylpyridinium chloride 5 (R = PhCO, X = Cl) yields selectively the stable 4-benzyl-3-ethoxycarbonyl-1,4-dihydropyridine 9.Treatment of 1-methyl- or 1-benzoyl-3-ethoxycarbonylpyridinium salts 5 with zinc and benzoyl chloride gives a mixture of products. 1-Methyl-2-ethoxycarbonylpyridinium iodide 11 (R = CH3, X = I) reacts with zinc and benzyl bromide giving, after catalytic hydrogenation, 2-, 4- and 6-benzyl-2-ethoxycarbonyl-1-methylpiperidines 12, 13 and 14 (R = CH3) in the ratio 2:7:1, but 1-benzyl-2-ethoxycarbonylpyridinium bromide 11 (R = PhCH2, X = Br) gives only 1,4-dibenzyl-2-ethoxycarbonylpiperidine 13 (R = PhCH2).

Bridged-ring Nitrogen Compounds. Part 5. Synthesis of 2,6-Methano-3-benzazonine ring-system

Syntheses of cis- and trans-4-benzyl- and 4-(3-methoxybenzyl)-2-methoxycarbonyl-1-methylpiperidines are described; amino-acids and amino-alcohols obtained from these compounds failed to cyclise. cis-2-Benzyl-4-ethoxycarbonyl-1-methylpiperidine has been ma