2,6-Dimethylpiperidine

{{chembox

|Verifiedfields = changed

|Watchedfields = changed

|verifiedrevid = 477212143

|Name = 2,6-Dimethylpiperidine

|ImageFile = Dimethylpiperidine.png

|ImageName = Structure of 2,6-dimethylpiperidine

|PIN = 2,6-Dimethylpiperidine

|OtherNames = 2,6-Lupetidine; nanofin; nanophyn

|Section1={{Chembox Identifiers

|SMILES = CC1CCCC(C)N1

|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

|ChemSpiderID = 62076

|InChI = 1/C7H15N/c1-6-4-3-5-7(2)8-6/h6-8H,3-5H2,1-2H3

|InChIKey = SDGKUVSVPIIUCF-UHFFFAOYAU

|SMILES1 = N1C(C)CCCC1C

|StdInChI_Ref = {{stdinchicite|correct|chemspider}}

|StdInChI = 1S/C7H15N/c1-6-4-3-5-7(2)8-6/h6-8H,3-5H2,1-2H3

|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

|StdInChIKey = SDGKUVSVPIIUCF-UHFFFAOYSA-N

|CASNo_Ref = {{cascite|changed|??}}

|CASNo = 504-03-0

|RTECS = OK5775000

|PubChem = 68843

|EC_number = 207-981-6

|UNII = 329I5805BP

|ChEMBL = 2104431

}}

|Section2={{Chembox Properties

|C=7 | H=15 | N=1

|Appearance = Colorless liquid

|Density = 0.84 g/mL

|Solubility = Low

|Solvent = other solvents

|SolubleOther = Most organic solvents

|BoilingPtC = 113.2

|pKb = ca. 10

|RefractIndex = 1.4394

}}

|Section7={{Chembox Hazards

|MainHazards = Flammable

|FlashPtC = 11

|GHSPictograms = {{GHS02}}{{GHS05}}{{GHS07}}

|GHSSignalWord = Danger

|HPhrases = {{H-phrases|225|314|315|319|335}}

|PPhrases = {{P-phrases|210|233|240|241|242|243|260|261|264|271|280|301+330+331|302+352|303+361+353|304+340|305+351+338|310|312|321|332+313|337+313|362|363|370+378|403+233|403+235|405|501}}

}}

|Section8={{Chembox Related

|OtherCompounds = Piperidine

}}

}}

2,6-Dimethylpiperidines are chemical compounds with the formula C₅H₈(CH₃)₂NH. Three stereoisomers exist: the achiral (R,S)-isomer and the chiral (R,R)/(S,S) enantiomeric pair. Dimethylpiperidines are derivatives of the heterocycle piperidine, wherein two hydrogen atoms are replaced by methyl groups.

The 2,6-dimethylpiperidines are prepared by reduction of 2,6-dimethylpyridine (2,6-lutidine). The achiral isomer is the predominant isomer produced in this reaction.

The 2,6-dimethylpiperidines are of interest for their conformational properties. The (R,S)-isomer exists largely in the chair conformation with equatorial methyl groups. The (R,R)/(S,S)-isomers are attractive chiral secondary amine building blocks.Einhorn, J.; Einhorn, C.; Ratajczak, F.; Durif, A.; Averbuch, M.-T. and Pierre, J.-L., "Synthesis and resolution of a chiral analog of 2,2,6,6-tetramethylpiperidine and of its corresponding nitroxide", Tetrahedron Letters, 1998, volume 39, pages 2565-2568