35794-11-7

Basic information

• Product Name: 3,5-Dimethylpiperidine
• Synonyms: Hexahydro-3,5-lutidine 3,5-Lupetidine;3,5-diMethylpiperidines;Piperidine,3,5-diMethyl-;3,5-DiMethylpiperidine, Mixture of cis and trans >=96%;3,5-Dimethylpiperidine,cis+trans,97%;3,5-DIMETHYLPIPERDINE;3,5-Dimethylpiperidine (cis- and trans- mixture);3,5-Dimethylpiperidine, cis and trans
• CAS NO: 35794-11-7
• Molecular Formula: C₇H₁₅N
• Molecular Weight: 113.2
• EINECS: 252-730-6
• Product Categories: Building Blocks;C5 to C7;Chemical Synthesis;Heterocyclic Building Blocks;Piperidines;Piperidine
• Mol File: 35794-11-7.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 144 °C(lit.)
• Flash Point: 91 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 0.853 g/mL at 25 °C(lit.)
• Vapor Pressure: 5.93mmHg at 25°C
• Refractive Index: n20/D 1.4454(lit.)
• Storage Temp.: Flammables area
• PKA: 10.52±0.10(Predicted)
• BRN: 102638
• CAS DataBase Reference: 3,5-Dimethylpiperidine(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Dimethylpiperidine(35794-11-7)
• EPA Substance Registry System: 3,5-Dimethylpiperidine(35794-11-7)

Safety Data

• Hazard Codes: Xi,F
• Statements: 10-36/37/38
• Safety Statements: 16-26-36/37/39-37/39-36
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 35794-11-7(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to light yellow liquid

Uses

Different sources of media describe the Uses of 35794-11-7 differently. You can refer to the following data:
1. Reactant for synthesis of: Substituted bisphenol A derivatives as β-amyloid peptide aggregation inhibitors1 MMP-13 selective isonipecotamide α-sulfone hydroxamates2 Gem-diamines for active organocatalysts for biodiesel production3 Benzimidazole inhibitors of the antigen receptor-mediated NF-κB4 Reactant for Mannich reactions to form Ru(II) complexes5
2. Reactant for synthesis of: Substituted bisphenol A derivatives as β-amyloid peptide aggregation inhibitors MMP-13 selective isonipecotamide α-sulfone hydroxamates Gem-diamines for active organocatalysts for biodiesel production Benzimidazole inhibitors of the antigen receptor-mediated NF-κB Reactant for Mannich reactions to form Ru(II) complexes

InChI:InChI=1/C7H15N/c1-6-3-7(2)5-8-4-6/h6-8H,3-5H2,1-2H3/p+1/t6-,7-/m0/s1

Synthetic route

3,5-Lutidine (591-22-0) → 3,5-dimethylpiperidine (35794-11-7)

Conditions	Yield
With palladium on activated charcoal; hydrogen; acetic acid at 20℃; under 760.051 Torr; for 24h; Time;	100%
Stage #1: 3,5-Lutidine With hydrogen; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In octane at 120℃; under 15001.5 Torr; for 22h; Stage #2: With water Catalytic behavior; chemoselective reaction;	76 %Chromat.
With 5% active carbon-supported ruthenium; hydrogen; acetic acid In water at 90℃; under 22502.3 Torr; for 8h; Reagent/catalyst; Time; Autoclave;	99.5 %Chromat.
With palladium on activated charcoal; hydrogen In ethanol at 150℃; under 71257.1 Torr; for 5h; Temperature; Pressure; Solvent;

3,5-dimethyl-piperidine-2,6-dione (25115-68-8) → 3,5-dimethylpiperidine (35794-11-7)

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether

meso-2,4-dimethylglutaric anhydride (4295-92-5, 7446-84-6, 35878-31-0, 50901-09-2, 82950-73-0, 118139-25-6) → 3,5-dimethylpiperidine (35794-11-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: ammonia 2: lithium alanate; diethyl ether View Scheme

3,5-dimethylpiperidine (35794-11-7) + 1,4-di-o-tosyl-2,3-isopropylidene-D-threitol (51064-65-4) → C21H40N2O2

Conditions	Yield
for 18h; Heating;	99%

3,5-dimethylpiperidine (35794-11-7) + (E)-3-phenylacrylic acid (140-10-3) → (E)-1-(3,5-dimethylpiperidin-1-yl)-3-phenylprop-2-en-1-one

Conditions	Yield
With 3,4,5-trifluorophenylboronic acid In xylene for 29h; Heating;	99%

3,5-dimethylpiperidine (35794-11-7) + 4-Phenylbutyric acid (1821-12-1) → 1-(3,5-Dimethyl-piperidin-1-yl)-4-phenyl-butan-1-one

Conditions	Yield
With 3,4,5-trifluorophenylboronic acid In toluene for 16h; Heating; other reagents;	99%
With 3,5-di-C10F21-C6H3-B(OH)2; 4 A molecular sieve In toluene for 15h; Heating;	95%
With boric acid In toluene for 15h; Dean-Stark; Reflux; Green chemistry; chemoselective reaction;	95%
With triethoxyantimony In toluene Acylation; Heating;	44%

3,5-dimethylpiperidine (35794-11-7) + MANDELIC ACID (611-71-2, 611-72-3, 17199-29-0, 90-64-2) → 1-(3,5-dimethylpiperidin-1-yl)-2-hydroxy-2-phenylethanone (1445918-79-5)

Conditions	Yield
With butylboronic acid; water; benzoic acid In toluene for 14h; Reagent/catalyst; Solvent; Temperature; Reflux;	99%
With [2-[(2,2,6,6-tetramethylpiperidin-1-yl)methyl]phenyl]boronic acid; benzoic acid In toluene for 16h; Reagent/catalyst; Time; Concentration; Solvent; Reflux; Molecular sieve;	99%

3,5-dimethylpiperidine (35794-11-7) + cyclohexenone (930-68-7) → rac-N-phenyl-3,5-dimethylpiperidine

Conditions	Yield
With PdCl2(PMePh2)2; oxygen; Potassium benzoate; benzoic acid In toluene at 20 - 100℃; for 18h; Sealed tube;	98%

3,5-dimethylpiperidine (35794-11-7) + 2-chloro-5-nitro-4'-chlorobenzophenone (70132-91-1) → [2-(3,5-dimethyl-1-piperidinyl)-5-nitrophenyl]-(4-chlorophenyl) methanone

Conditions	Yield
With calcium carbonate In ethanol	97%

3,5-dimethylpiperidine (35794-11-7) → 2-(3,5-dimethyl-piperidin-1-ylsulfanyl)-benzothiazole (32997-30-1)

Conditions	Yield
	97%

3,5-dimethylpiperidine (35794-11-7) + 2-phenyl-1,3,4-oxadiazole (825-56-9) → N'-[(3,5-dimethylpiperidin-1-yl)methylidene]benzohydrazide (1323158-97-9)

Conditions	Yield
at 80℃; for 5.5h;	97%

3,5-dimethylpiperidine (35794-11-7) + dimethyl sulfate (77-78-1) → N,N-dimethyl-3,5-dimethylpiperidinium hydroxide

Conditions	Yield
Stage #1: 3,5-dimethylpiperidine; dimethyl sulfate In toluene at 0 - 70℃; for 1h; Large scale; Stage #2: dimethyl sulfate With sodium hydroxide In water; toluene at 5 - 50℃; Large scale; Further stages;	97%

3,5-dimethylpiperidine (35794-11-7) + 5-chloro-2-fluorobenzonitrile (57381-34-7) → 5-chloro-2-(3,5-dimethyl-piperidin-1-yl)-benzonitrile (660831-14-1)

Conditions	Yield
With caesium carbonate In DMF (N,N-dimethyl-formamide) at 80℃; for 12h;	96%

3,5-dimethylpiperidine (35794-11-7) + benzoic acid (65-85-0) → (3,5-dimethylpiperidin-1-yl)(phenyl)methanone (121882-68-6)

Conditions	Yield
With 3,4,5-trifluorophenylboronic acid In 1,3,5-trimethyl-benzene for 20h; Heating;	95%
With boric acid In o-xylene for 20h; Dean-Stark; Reflux; Green chemistry; chemoselective reaction;	85%
With dichloro(dimethylglyoxime)(dimethylglyoximato)cobalt(III); [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; triphenylphosphine In dichloromethane at 20℃; for 12h; Inert atmosphere; Sealed tube; Irradiation;	66%

3,5-dimethylpiperidine (35794-11-7) + 1-(3'-carboxy-2'-fluoro-biphenyl-3-yl)-5-cyclopropyl-1H-pyrazole-4-carboxylic acid methyl ester → 5-cyclopropyl-1-[3'-(3,5-dimethyl-piperidine-1-carbonyl)-2'-fluoro-biphenyl-3-yl]-1H-pyrazole-4-carboxylic acid methyl ester

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane for 16h;	95%

3,5-dimethylpiperidine (35794-11-7) + 4-fluoro-3-nitrobenzaldehyde (42564-51-2) → 4-(3,5-dimethylpiperidin-1-yl)-3-nitro-benzaldehyde

Conditions	Yield
In dichloromethane at 0 - 20℃; for 0.5h;	93.5%
With triethylamine In dichloromethane at 20℃; for 0.5h; Cooling with ice;	93%

3,5-dimethylpiperidine (35794-11-7) + ethyl 6-chloro-7-fluoro-2-(trifluoromethyl)-2H-1-benzopyran-3-carboxylate (264879-17-6) → ethyl 6-chloro-7-(3,5-dimethylpiperidin-1-yl)-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Conditions	Yield
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 90℃; for 48h;	93%

Upstream product

• 25115-68-8 3,5-dimethyl-piperidine-2,6-dione 
• 591-22-0 3,5-Lutidine 
• 67-56-1 methanol 
• 4295-92-5 meso-2,4-dimethylglutaric anhydride 

Downstream Products

• 1034257-10-7 (2-amino-5-bromophenyl)((3R,5S)-3,5-dimethylpiperidin-1-yl)methanone 
• 1044749-58-7 3-(4-{[3-(3,5-dimethyl-1-piperidinyl)propyl]oxy}phenyl)-2-methyl-4(3H)-quinazolinone 
• 1323158-97-9 N'-[(3,5-dimethylpiperidin-1-yl)methylidene]benzohydrazide 
• 1205080-59-6 C₁₄H₂₁N 
• 780-25-6 N-benzylidene benzylamine 
• 103-49-1 dibenzylamine 
• 1449376-11-7 2,2-dichloro-1-(4-ethoxyphenyl)cyclopropanyl-3,5-dimethylpiperidin-1-yl ketone 
• 1200127-06-5 3-(4-(((3R,5S)-3,5-dimethylpiperidin-1-yl)methyl)phenyl)-9Hpyrrolo[2,3-b:5,4-c′]-dipyridine-6-carbonitrile 
• 68291-25-8 3,5-dimethylpiperidine-1-carbaldehyde 
• 158890-34-7 N-Chloroacetyl-3,5-dimethylpiperidine 

Relevant articles and documents

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HYDROGENATION PROCESS

A process for the production of heterocyclic quaternary ammonium salts or hydroxides is disclosed. The process comprises a continuous hydrogenation step, in which an unsaturated heterocyclic amine is reacted with hydrogen to form a saturated heterocyclic amine; a first continuous N-alkylation step, in which the saturated heterocyclic amine is alkylated to produce an intermediate saturated heterocyclic amine having an increased degree of substitution compared to the saturated heterocyclic amine; and one or more further N-alkylation steps in which the intermediate saturated heterocyclic amine is N-alkylated to the heterocyclic quaternary ammonium salt or hydroxide. A process of producing a saturated heterocyclic amineis also disclosed. The process comprises reacting an unsaturated heterocyclic amine with hydrogen in a vapour phase reaction at a pressure of not more than 70 bar and a temperature in the range of from 150°C to 350°C. A process of N-alkylating a saturated heterocyclic amine is also disclosed. The process comprises N-alkylating the saturated heterocyclic amine in a vapour phase reaction at a temperature of at least 2°C.

Cobalt-bridged secondary building units in a titanium metal-organic framework catalyze cascade reduction of N-heteroarenes

We report here a novel Ti3-BPDC metal-organic framework (MOF) constructed from biphenyl-4,4′-dicarboxylate (BPDC) linkers and Ti3(OH)2 secondary building units (SBUs) with permanent porosity and large 1D channels. Ti-OH groups from neighboring SBUs point toward each other with an O-O distance of 2 ?, and upon deprotonation, act as the first bidentate SBU-based ligands to support CoII-hydride species for effective cascade reduction of N-heteroarenes (such as pyridines and quinolines) via sequential dearomative hydroboration and hydrogenation, affording piperidine and 1,2,3,4-tetrahydroquinoline derivatives with excellent activity (turnover number ～ 1980) and chemoselectivity.