89873-67-6

Basic information

• Product Name: 2-Pyridinecarbonitrile, 1,2,3,6-tetrahydro-1-(phenylmethyl)-
• CAS NO: 89873-67-6
• Molecular Formula: C13H14N2
• Molecular Weight: 198.268
• Mol File: 89873-67-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 2-Pyridinecarbonitrile, 1,2,3,6-tetrahydro-1-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Pyridinecarbonitrile, 1,2,3,6-tetrahydro-1-(phenylmethyl)-(89873-67-6)
• EPA Substance Registry System: 2-Pyridinecarbonitrile, 1,2,3,6-tetrahydro-1-(phenylmethyl)-(89873-67-6)

Safety Data

• Hazardous Substances Data: 89873-67-6(Hazardous Substances Data)

Upstream product

• 85617-07-8 (+/-)-1-benzyl-2-cyano-3-piperideine 
• 100-39-0 benzyl bromide 
• 110-86-1 pyridine 
• 773837-37-9 sodium cyanide 
• 26872-08-2 N-benzylpyridinium hexafluorophosphate 
• 2589-31-3 N-benzylpyridinium bromide 
• 89873-51-8 1-benzyl-1,2,5,6-tetrahydropyridine-N-oxide 
• 40240-12-8 1-benzyl-1,2,3,6-tetrahydropyridine 

Downstream Products

• 31608-18-1 (R)-(-)-coniine (S)-(+)-mandelic acid salt 
• 98195-27-8 1-benzyl-2-n-propylpiperidine 
• 120153-71-1 2-(3,4-Dimethoxy-benzoyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid phenyl ester 
• 120153-74-4 (1R,8aR)-1-(3,4-Dimethoxy-phenyl)-1,5,8,8a-tetrahydro-oxazolo[3,4-a]pyridin-3-one 
• 120153-76-6 (S)-(3,4-Dimethoxy-phenyl)-(S)-1,2,3,6-tetrahydro-pyridin-2-yl-methanol 
• 793631-29-5 (1-Benzyl-1,2,3,6-tetrahydro-pyridin-2-yl)-(3,4-dimethoxy-phenyl)-methanone 

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