153198-06-2

Basic information

• Product Name: Tert-Butyl 4-(2,2,2-trifluoroacetamido)piperidine-1-carboxylate
• Synonyms: Tert-Butyl 4-(2,2,2-trifluoroacetamido)piperidine-1-carboxylate
• CAS NO: 153198-06-2
• Molecular Formula: C₁₂H₁₉F₃N₂O₃
• Molecular Weight: 296.2860696
• Mol File: 153198-06-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Tert-Butyl 4-(2,2,2-trifluoroacetamido)piperidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Tert-Butyl 4-(2,2,2-trifluoroacetamido)piperidine-1-carboxylate(153198-06-2)
• EPA Substance Registry System: Tert-Butyl 4-(2,2,2-trifluoroacetamido)piperidine-1-carboxylate(153198-06-2)

Safety Data

• Hazardous Substances Data: 153198-06-2(Hazardous Substances Data)

Upstream product

• 124830-45-1 tert-butyl 4-aminocyclohexanecarboxylate 
• 383-63-1 ethyl trifluoroacetate, 
• 87120-72-7 1-(tert-butoxycarbonyl)-4-aminopiperidine 
• 97181-50-5 N-(1-benzyl-4-piperidinyl)-2,2,2-trifluoroacetamide 
• 50541-93-0 4-amino-1-benzylpiperidine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 97181-51-6 4-trifluoromethylcarbonylamino piperidine 

Downstream Products

• 309251-30-7 4-(2-fluorophenyl)acetamidopiperidine 
• 153198-08-4 5-bromo-2,3-dimethoxy-N-(piperidin-4-yl)benzamide 
• 153198-07-3 5-bromo-2,3-dimethoxy-N-<1-(tert-butyloxycarbonyl)piperidin-4-yl>benzamide 
• 87120-72-7 1-(tert-butoxycarbonyl)-4-aminopiperidine 

Relevant articles and documents

METHODS AND COMPOUNDS FOR TREATMENT OF LYMPHOCYTE-RELATED DISEASES AND CONDITIONS

Methods for treatment of lymphocyte-related diseases and conditions, such as cancer and automimmune diseases, are provided. The methods comprise administration of an effective amount of an oligomer to a patient in need thereof, wherein the oligomer comprises, inter alia, at least one intersubunit linkage having the following structure: wherein R1, L1, X, Y and Z are as defined herein.

OLIGONUCLEOTIDE ANALOGUES HAVING MODIFIED INTERSUBUNIT LINKAGES AND/OR TERMINAL GROUPS

Oligonucleotide analogues comprising modified intersubunit linkages and/or modified 3'' and/or 5''-end groups are provided. The disclosed compounds are useful for the treatment of diseases where inhibition of protein expression or correction of aberrant mRNA splice products produces beneficial therapeutic effects.

Mild deprotection of primary N-(p-toluenesulfonyl) amides with SmI 2 following trifluoroacetylation

A mild deprotection method for notoriously difficult to unmask primary N-(p-toluenesulfonyl) amides was developed during our total synthesis studies toward the marine toxin, gymnodimine. The deprotection occurs at low temperature (-78 °C) under mild conditions by initial activation of the nitrogen with a trifluoroacetyl group, followed by reductive cleavage of the p-toluenesulfonyl group with samarium diiodide. The substrate scope and functional group tolerance of this useful N-S cleavage process, which builds on related cleavage processes of other nitrogen-heteroatom bonds, is explored. Georg Thieme Verlag Stuttgart.

Synthesis and structure-activity relationships of N-(1-benzylpiperidin-4-yl)arylacetamide analogues as potent σ1receptor ligands

A series of N-(1-benzylpiperidin-4-yl)arylacetamides were synthesized and evaluated for their binding properties for σ1 and σ2 receptors. In agreement with previously reported σ1/σ2 receptor binding data for N-(1-benzylpiperidin-4-yl)phenylacetamide, all of the N-(1-benzylpiperidin-4-yl)arylacetamide compounds reported below displayed higher affinity for σ1 vs σ1 receptors. Replacement of the phenyl ring of the phenylacetamide moiety with a thiophene, naphthyl, or indole aromatic ring had no significant effect on the σ1 receptor affinity. Replacement of the phenyl ring with an imidazole or pyridyl aromatic ring resulted in a >60-fold loss in affinity for σ1 receptors and no significant binding affinity for σ2 receptors. Substitution on the aromatic ring of the benzyl group showed a similar or slightly decreased affinity for σ1 receptors. Substitution on the aromatic rings of both the phenylacetamide moiety and the benzyl group with a halogen resulted in a similar affinity for σ1 receptors and a significantly increased affinity for σ2 receptors. Comparative molecular field analysis revealed that electrostatic properties of the substituents in the phenylacetamide aromatic ring strongly influenced binding to σ1 receptors. Compounds 1, 10, 18, 22, 37, and 40 showed the highest selectivity for σ1 receptors with Ki (σ2) to Ki (σ1) ratios of 100, >92, >122, 77, 74, and 80, respectively. In agreement with previously reported results, the phenylacetamide analogues had no binding affinity for dopamine receptors (D2/D3).

18F-labeled benzamides for studying the dopamine D2 receptor with positron emission tomography

Two series of (N-benzylpiperidin-4-yl)- and (9-azabicyclo[3.3.1]nonan- 3β-yl)benzamides were prepared, and in vitro binding assays were used to measure the affinity of these compounds for dopamine D2, dopamine D3, serotonin 5-HT2, and α2-adrenergic receptors. The results of these studies indicated compounds 23, 26b, and 34 have the selectivity needed for in vivo studies of the D2 (and possibly D3) receptors. 18F-Labeled analogues of 23, 26b and 34 were prepared by N-alkylation of the corresponding desbenzyl precursors with [18F]-4-fluorobenzyl iodide. Preliminary in vivo studies demonstrated that [18F]-23 and [18F]-26b are suitable candidates for further evaluation in positron emission tomography imaging studies. The slow rate of washout of [18F]-34 from nondopaminergic regions and its comparatively high lipophilicity indicates that this compound may not be suitable for imaging studies because of a high level of nonspecific binding.