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

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

Uses

Used in Pharmaceutical Industry:
3,5-Dimethylpiperidine is used as a reactant for the synthesis of various pharmaceutical compounds, including substituted bisphenol A derivatives, which act as β-amyloid peptide aggregation inhibitors. These inhibitors are crucial for the development of drugs targeting neurodegenerative diseases such as Alzheimer's.
Used in Biochemical Research:
In the field of biochemical research, 3,5-Dimethylpiperidine serves as a reactant for the synthesis of MMP-13 selective isonipecotamide α-sulfone hydroxamates. These hydroxamates are essential for studying the role of matrix metalloproteinases in various biological processes and diseases.
Used in Organic Synthesis:
3,5-Dimethylpiperidine is used as a reactant for the synthesis of gem-diamines, which are active organocatalysts for biodiesel production. These organocatalysts play a significant role in the development of sustainable and environmentally friendly fuel alternatives.
Used in Immunology:
In the field of immunology, 3,5-Dimethylpiperidine is used as a reactant for the synthesis of benzimidazole inhibitors of the antigen receptor-mediated NF-κB pathway. These inhibitors are vital for understanding the regulation of immune responses and the development of immunomodulatory drugs.
Used in Coordination Chemistry:
3,5-Dimethylpiperidine also serves as a reactant for Mannich reactions to form Ru(II) complexes. These complexes are of interest in coordination chemistry and have potential applications in catalysis and materials science.

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 
• 4295-92-5 meso-2,4-dimethylglutaric anhydride 
• 591-22-0 3,5-Lutidine 
• 67-56-1 methanol 

Downstream Products

• 121836-28-0 2,6-bis(3',5'-dimethylpiperidin-1'-ylmethyl)-4-nitrophenol 
• 157831-72-6 4-chloro-6-(3',5'-dimethylpiperidin-1'-ylmethyl)-2-nitrophenol 
• 78755-19-8 4-(3,5-dimethylpiperidino)-1(2H)-phthalazinone 
• 69776-14-3 phthalazonyl glycol ether 
• 72811-68-8 4-m-Tolylamino-pyridine-3-sulfonic acid (3,5-dimethyl-piperidine-1-carbonyl)-amide 
• 121882-68-6 (3,5-dimethylpiperidin-1-yl)(phenyl)methanone 
• 127413-44-9 4,6-bis(3',5'-dimethylpiperidin-1'-ylmethyl)-2-nitrophenol 
• 876716-58-4 2-(3,5-Dimethyl-piperidin-1-yl)-ethylamine 

Relevant articles and documents

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PROBLEM TO BE SOLVED: To provide an industrially simple production method of a cyclic compound. SOLUTION: A production method of a cyclic compound includes a step to obtain a reduced form (B) by reducing an unsaturated bond in a ring structure of an aromatic compound (A) by means of catalytic hydrogenation of the aromatic compound (A) or its salt using palladium carbon as a catalyst under a normal pressure, in which the aromatic compound (A) has one or more ring structures selected from a group consisting of a five membered-ring, a six membered-ring, and a condensed ring of the five membered-ring or the six membered-ring with another six membered-ring, a hetero atom can be included in the ring structure, and the aromatic compound (A) can have one or two side chains bonded to the ring structure and does not have any carbon-carbon triple bond in the side chain. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

Method for synthesizing dimethylpiperidine

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