26977-07-1

Basic information

• Product Name: (+/-)-1-phenyl-4-(phenylamino)butanol
• Synonyms: (+/-)-1-phenyl-4-(phenylamino)butanol
• CAS NO: 26977-07-1
• Molecular Weight: 241.333
• Mol File: 26977-07-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (+/-)-1-phenyl-4-(phenylamino)butanol(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-1-phenyl-4-(phenylamino)butanol(26977-07-1)
• EPA Substance Registry System: (+/-)-1-phenyl-4-(phenylamino)butanol(26977-07-1)

Safety Data

• Hazardous Substances Data: 26977-07-1(Hazardous Substances Data)

Upstream product

• 56139-59-4 4-oxo-4-phenyl-butyraldehyde 
• 98-95-3 nitrobenzene 
• 62-53-3 aniline 
• 83-25-0 N-phenylmaleimide 
• 1955-39-1 5-phenyl-3H-furan-2-one 
• 55467-95-3 N-(3-chloropropyl)-benzeneamine 
• 3240-29-7 1-Phenylpent-4-en-1-one 
• 79913-35-2 3,6-diphenyl-5,6-dihydro-4H-[1,2]oxazine 
• 17649-94-4 N-phenyl 3-benzoylpropionamide 

Relevant articles and documents

N-phenyl-substituted pyrrolidines, piperidines and azabicyclics by a tandem reduction-double reductive amination reaction

N-Phenyl-substituted pyrrolidines and piperidines have been synthesized by catalytic reduction of nitrobenzene in the presence of 4- and 5-oxoaldehydes, respectively. The process involves reduction of the aromatic nitro group to give the N-phenylhydroxylamine or aniline followed by reductive amination with the two carbonyl functional groups. Monocyclic systems are generally formed in high yield and are easily purified. The method has also been extended to the synthesis of fused N-phenylazabicyclics from 2-(3-oxopropyl)cycloalkanones. A high degree of diastereoselectivity for the trans-fused product is observed in substrates having an ester group α to the cycloalkanone carbonyl. Bicyclic precursors lacking this ester group give mixtures of cis and trans products. Finally, contrary to previous reports, we have demonstrated that aniline can be substituted for nitrobenzene in these reactions.

Reductive Transformations of 5,6-Dihydro-4H-1,2-oxazines: Synthesis of 4-Hydroxy Ketoximes, N-Hydroxypyrrolidine Derivatives, and Other Nitrogen-Containing Compounds

6-Siloxy-substituted 1,2-oxazines 1 are transformed into 4-hydroxy ketoximes 2 by reduction with NaBH4 in ethanol.Reductive Beckmann rearrangement converts the oxime 2a into the 1,4-amino alcohol 7.Diisobutylaluminum hydride (DIBAH) induces a novel reductive ring contraction of 1 to provide either N-hydroxypyrrolidine derivatives 8 or nitrones 9.Other 1,2-oxazines lacking the 6-siloxy substituent are also studied under these reaction conditions.Catalytic hydrogenolysis either gives the acyclic amine 16 or it stops at the stage of the proline derivative 21.Mechanistic features of these synthetically valuable transfomations are discussed.