1-Boc-4-(aminomethyl)piperidine
Need Assistance?
  • US & Canada:
    +
  • UK: +

1-Boc-4-(aminomethyl)piperidine

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

1-Boc-4-(aminomethyl)piperidine is a protected 4-substituted piperidinecarboxylate used in the preparation of orally active platelet-activating factor antagonists as well as other biologically active compounds.

Category
BOC-Amino Acids
Catalog number
BAT-007782
CAS number
144222-22-0
Molecular Formula
C11H22N2O2
Molecular Weight
214.28
1-Boc-4-(aminomethyl)piperidine
IUPAC Name
tert-butyl 4-(aminomethyl)piperidine-1-carboxylate
Synonyms
Boc-4-(aminomethyl)piperidine; Piperidin-4-ylmethyl-carbamic acid tert-butyl ester; 1-Boc-4-(aminomethyl)piperidine; tert-butyl 4-(aminomethyl)piperidine-1-carboxylate; 4-(Aminomethyl)-1-N-Boc-piperidine; 4-Aminomethyl-1-Boc-piperidine; 1-n-boc-4-(aminomethyl)piperidine; 4-aminomethyl-piperidine-1-carboxylic acid tert-butyl ester; 1-Piperidinecarboxylic acid, 4-(aminomethyl)-, 1,1-dimethylethyl ester
Appearance
White to yellow low melting solid
Purity
≥ 98 % (HPLC)
Density
1.013 g/mL at 25 ℃
Boiling Point
237.0-238.0 ℃
Storage
Store at 2-8 ℃
InChI
InChI=1S/C11H22N2O2/c1-11(2,3)15-10(14)13-6-4-9(8-12)5-7-13/h9H,4-8,12H2,1-3H3
InChI Key
KLKBCNDBOVRQIJ-UHFFFAOYSA-N
Canonical SMILES
CC(C)(C)OC(=O)N1CCC(CC1)CN
1. Semi-Rigid (Aminomethyl) Piperidine-Based Pentadentate Ligands for Mn(II) Complexation
Jonathan Martinelli, Edoardo Callegari, Zsolt Baranyai, Alberto Fraccarollo, Maurizio Cossi, Lorenzo Tei Molecules. 2021 Oct 2;26(19):5993. doi: 10.3390/molecules26195993.
Two pentadentate ligands built on the 2-aminomethylpiperidine structure and bearing two tertiary amino and three oxygen donors (three carboxylates in the case of AMPTA and two carboxylates and one phenolate for AMPDA-HB) were developed for Mn(II) complexation. Equilibrium studies on the ligands and the Mn(II) complexes were carried out using pH potentiometry, 1H-NMR spectroscopy and UV-vis spectrophotometry. The Mn complexes that were formed by the two ligands were more stable than the Mn complexes of other pentadentate ligands but with a lower pMn than Mn(EDTA) and Mn(CDTA) (pMn for Mn(AMPTA) = 7.89 and for Mn(AMPDA-HB) = 7.07). 1H and 17O-NMR relaxometric studies showed that the two Mn-complexes were q = 1 with a relaxivity value of 3.3 mM-1 s-1 for Mn(AMPTA) and 3.4 mM-1 s-1 for Mn(AMPDA-HB) at 20 MHz and 298 K. Finally, the geometries of the two complexes were optimized at the DFT level, finding an octahedral coordination environment around the Mn2+ ion, and MD simulations were performed to monitor the distance between the Mn2+ ion and the oxygen of the coordinated water molecule to estimate its residence time, which was in good agreement with that determined using the 17O NMR data.
2. (2S)-1-(arylacetyl)-2-(aminomethyl)piperidine derivatives: novel, highly selective kappa opioid analgesics
V Vecchietti, A Giordani, G Giardina, R Colle, G D Clarke J Med Chem. 1991 Jan;34(1):397-403. doi: 10.1021/jm00105a061.
This paper describes the synthesis and structure-activity relationships as kappa opioid analgesics of a novel class of 1-(arylacetyl)-2-(aminomethyl)piperidine derivatives. The active conformation of the pharmacophore, with a torsional angle (N1C2C7N8) of 60 degrees, was defined with computational studies and 1H NMR. A quantitative structure-activity relationship study of the arylacetic moiety substitution indicated that the presence of an electron-withdrawing and lipophilic substituent in para and/or meta positions is required for good analgesic activity and kappa affinity. The lead compounds (2S)-1-[(3,4-dichlorophenyl)acetyl]-2-(pyrrolidin-1-ylmethyl )piperidine hydrochloride and (2S)-1-[4-(trifluoromethyl)phenyl]acetyl]-2-(pyrrolidin-1-ylmet hyl) piperidine hydrochloride are the most kappa/mu selective (respectively 6500:1 and 4100:1) and among the most potent (Ki kappa 0.24 and 0.57 nM, respectively) kappa ligands identified so far. In the mouse tail flick model of antinociception, compound 14 (ED50 = 0.05 mg/kg sc) was 25 times more potent than morphine and 16 times more potent than the standard kappa ligand U-50488.
3. Aminopiperidine based complexes for lactide polymerisation
P McKeown, M G Davidson, J P Lowe, M F Mahon, L H Thomas, T J Woodman, M D Jones Dalton Trans. 2016 Mar 28;45(12):5374-87. doi: 10.1039/c5dt04695e.
Herein we report the synthesis and characterisation of a series of salalen and salan ligands derived from 2-(aminomethyl)piperidine. Depending on the choice of starting salicylaldehyde, a bicyclic salan type ligand (1-3H2) or imino salalen type ligand (4-6H, 7-9H2) were prepared. The ligands were successfully complexed to group 4 metals and aluminium; with hafnium and zirconium octahedral complexes, M(1-3)2, were realised; whilst with aluminium tetrahedral and trigonal bipyramidal complexes, Al(1-9)Mex (x = 1,2), were isolated. The complexes have been characterised in solution via(1)H and (13)C{(1)H} NMR spectroscopy and in the solid state by X-ray crystallography. The group 4 complexes were observed to have a fac-fac arrangement of ligands and there were two isomers present when 3H2 was ligated. The imino aluminium complexes Al(7-9)Me were isolated as a mixture of diastereoisomers. The resultant complexes were trialed in the ring opening polymerisation of rac-lactide with both heterotactic and isotactic PLA being demonstrated. Tacticity was found to be dependent on the nature of the ligand and metal used; the M(1-3)2 complexes were generally found to have a heterotactic preference (Pr = 0.67-0.76) and the aluminium polymerisation outcome was dictated more by the steric influence of the ligand, particularly for Al(4/6)Me2/Al(7/9)Me.
Online Inquiry
Verification code
Inquiry Basket