206273-84-9

Basic information

• Product Name: tert-butyl 4-(4-methoxybenzylamino)piperidine-1-carboxylate
• Synonyms: tert-butyl 4-(4-methoxybenzylamino)piperidine-1-carboxylate
• CAS NO: 206273-84-9
• Molecular Formula: C₁₈H₂₈N₂O₃
• Molecular Weight: 320.42652
• Mol File: 206273-84-9.mol

Chemical Properties

• Boiling Point: 433.3±40.0 °C(Predicted)
• Appearance: /
• Density: 1.09±0.1 g/cm3(Predicted)
• PKA: 9.59±0.20(Predicted)
• CAS DataBase Reference: tert-butyl 4-(4-methoxybenzylamino)piperidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 4-(4-methoxybenzylamino)piperidine-1-carboxylate(206273-84-9)
• EPA Substance Registry System: tert-butyl 4-(4-methoxybenzylamino)piperidine-1-carboxylate(206273-84-9)

Safety Data

• Hazardous Substances Data: 206273-84-9(Hazardous Substances Data)

Upstream product

• 87120-72-7 1-(tert-butoxycarbonyl)-4-aminopiperidine 
• 123-11-5 4-methoxy-benzaldehyde 
• 104-92-7 1-bromo-4-methoxy-benzene 

Downstream Products

• 1091682-33-5 [1-((S)-2-amino-3,3-dimethyl-butyryl)-piperidin-4-yl]-(4-methoxy-benzyl)-carbamic acid benzyl ester hydrochloride 
• 1091682-32-4 (R)-2-cyclopentylmethyl-3-(formyl-hydroxy-amino)-N-{(S)-1-[4-(4-methoxy-benzylamino)-piperidine-1-carbonyl]-2,2-dimethyl-propyl}-propionamide 

Relevant articles and documents

Identification of novel aminopiperidine derivatives for antibacterial activity against Gram-positive bacteria

We have previously reported amidopiperidine derivatives as a novel peptide deformylase (PDF) inhibitor and evaluated its antibacterial activity against Gram-positive bacteria, but poor pharmacokinetic profiles have resulted in low efficacy in in vivo mouse models. In order to overcome these weaknesses, we newly synthesized aminopiperidine derivatives with remarkable antimicrobial properties and oral bioavailability, and also identified their in vivo efficacy against methicillin-resistant Staphylococcus aureus (MRSA), vancomycin-resistant Enterococcus (VRE) and penicillin-resistant Streptococcus pneumoniae (PRSP).

Rapid and efficient access to secondary arylmethylamines

Ammoniomethyl trifluoroborates are very powerful reagents that can be used to access biologically relevant aryl- and heteroaryl-methylamine motifs via Suzuki-Miyaura cross-couplings. Until now, this method was limited to the production of tertiary and primary amines. The synthesis of a large array of secondary ammoniomethyltrifluoroborates has been achieved through a one step nucleophilic substitution reaction on the potassium bromomethyltrifluoroborate. Smooth cross-coupling conditions have been designed, based on the use of an aminobiphenyl palladium precatalyst, to couple these trifluoroborates efficiently with aryl bromides. This strategy offers a new way to access biologically relevant motifs and allows, with the previously developed methods, access to all three classes of aminomethylarenes. Secondary ammoniomethyltrifluoroborates can be easily synthesized by nucleophilic substitution on potassium bromomethyltrifluoroborate. These reagents have then been used in Suzuki-Miyaura cross-couplings with aryl bromides, offering an effective access to the aminomethylarene structural motif. This new method provides an interesting alternative to the reductive amination procedure (see scheme). Copyright