98195-27-8

Basic information

• Product Name: 1-benzyl-2-propylpiperidine
• CAS NO: 98195-27-8
• Molecular Formula: C₁₅H₂₃N
• Molecular Weight: 217.3498
• Mol File: 98195-27-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 294.3°C at 760 mmHg
• Flash Point: 120.3°C
• Density: 0.945g/cm³
• Vapor Pressure: 0.00164mmHg at 25°C
• Refractive Index: 1.518
• CAS DataBase Reference: 1-benzyl-2-propylpiperidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-benzyl-2-propylpiperidine(98195-27-8)
• EPA Substance Registry System: 1-benzyl-2-propylpiperidine(98195-27-8)

Safety Data

• Hazardous Substances Data: 98195-27-8(Hazardous Substances Data)

Upstream product

• 100-44-7 benzyl chloride 
• 3238-60-6 rac-coniine 
• 4783-65-7 N-benzyl-2-piperidinone 
• 927-77-5 n-propylmagnesium bromide 
• 2589-31-3 N-benzylpyridinium bromide 
• 100-39-0 benzyl bromide 
• 110-86-1 pyridine 
• 89873-67-6 1-benzyl-1,2,3,6-tetrahydropyridine-2-carbonitrile 
• 26872-08-2 N-benzylpyridinium hexafluorophosphate 
• 98195-08-5 1-benzyl-2,6-dicyanopiperidine 
• 120153-68-6 N-benzylpiperidine-2-carbonitrile 
• 98195-12-1 1-benzyl-2,6-dicyano-2-propylpiperidine 

Downstream Products

• 15991-59-0 2-propylpiperidine hydrochloride 
• 31608-18-1 (R)-(-)-coniine (S)-(+)-mandelic acid salt 
• 81076-52-0 (3R^*,5S^*,9S^*)-gephyrotoxin 223AB 
• 81076-50-8 gephyrotoxin 223AB 
• 86963-79-3 1-Benzyl-6-propyl-piperidine-2-carbonitrile 
• 3238-60-6 rac-coniine 

Relevant articles and documents

Modified fry cyanation of a chiral pyridinium salt: Asymmetric syntheses of (-)-coniine and (-)-solenopsin A

The synthesis of chiral 2-cyano-Δ4-tetrahydropyridine 5 was carried out in 85 % yield through a modified two-step Fry reductive cyanation of pyridinium salt (+)-3c that used lithium triethylborohydride as the hydride donor. An alkylation-reduction sequence provided 2-alkyl-substituted tetrahydropyridines (+)-10a and (+)-10b in 72-75 % yield after chromatographic purification. This protocol has been applied to the asymmetric syntheses of piperidine alkaloids (-)-coniine and (-)-solenopsin A. The two-step reductive cyanation of chiral pyridinium salt (+)-3c afforded α-amino nitrile 5 in 85 % yield, which underwent an alkylation-reduction sequence followed by removal of the chiral moiety to yield the hemlock alkaloid (-)-coniine as its mandelate salt (>99:1 er). This reaction sequence was also used for the synthesis of the trans-2,6-disubstituted piperidine alkaloid (-)-solenopsin A. Copyright

Versatile one-pot reductive alkylation of lactams/amides via amide activation: Application to the concise syntheses of bioactive alkaloids (±)-bgugaine, (±)-coniine, (+)-preussin, and (-)-cassine

Direct entry: One-pot reductive alkylation of lactams/amides with Grignard reagents has been realized via lactam/amide activation with Tf2O. This method opens a direct entry to α-alkylated amines. The versatility of the method is illustrated by the concise syntheses of bioactive alkaloids (±)-bgugaine, (±)-coniine, (+)-preussin, and (?)-cassine.

Efficient and Convenient Method for Synthesis of Solenopsin A and Its Analogues Using 1-Benzyl-2,6-dicyanopiperidine

An efficient synthetic sequence proposed here provides a new method for preparation of not only solenopsin A, i.e., trans-2-methyl-6-undecylpiperidine, but also coniine, i.e., 2-propylpiperidine, and other 2,6-dialkylpiperidine alkaloids: A reaction of 1-benzyl-2,6-dicyanopiperidine (1) with alkyl halides selectively gives 2-alkyl- and 2,6-dialkyl-1-benzyl-2,6-dicyanopiperidines (2 and 3), decyanation of which affords respectively 2-alkyl- and 2,6-dialkyl-1-benzylpiperidines (4 and 5) in high yields.