22990-77-8

Basic information

• Product Name: 2-PIPERIDYLMETHYLAMINE
• Synonyms: 1-(Piperidin-2-yl)methylamine;1-piperidin-2-ylmethanamine;2-AMINOMETHYL PIPERIDINE 99%;Piperidine-2-methanamine;piperidin-2-ylmethanamine;2-PIPERIDYLMETHYLAMI;2 - Methyl piperidine aMMonia;(RS)-1-(Piperidin-2-yl)methanamine
• CAS NO: 22990-77-8
• Molecular Formula: C₆H₁₄N₂
• Molecular Weight: 114.19
• EINECS: 245-371-1
• Product Categories: Piperidines, Piperidones, Piperazines;Piperidine;Amines;Piperazine;Building Blocks;Heterocyclic Building Blocks;Piperidines
• Mol File: 22990-77-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 63-66°C/12mm
• Flash Point: 63-66°C/12mm
• Appearance: Colorless clear liquid.
• Density: 0.9406 g/mL at 25 °C
• Vapor Pressure: 1.07mmHg at 25°C
• Refractive Index: 1.4850
• Storage Temp.: -20°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: 10.32±0.29(Predicted)
• BRN: 102994
• CAS DataBase Reference: 2-PIPERIDYLMETHYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PIPERIDYLMETHYLAMINE(22990-77-8)
• EPA Substance Registry System: 2-PIPERIDYLMETHYLAMINE(22990-77-8)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: 2735
• WGK Germany: 2
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 22990-77-8(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 22990-77-8 differently. You can refer to the following data:
1. 2-Piperidinemethanamine is used in the synthesis of compounds exhibiting anti-osteoclast and anti-osteoblast activity. It also is used in the synthesis of potent antibacterial.
2. Reactant for reversible aminal formationReactant for synthesis of:Annulated N-heterocyclic carbene ligandsM3 Muscarinic receptor antagonistsSelective 5-ht5A receptor antagonistsTernary platinum(II) complexes

Purification Methods

Dry (over Na2SO4) and distil the piperidine under vacuum from KOH. It has been purified via the Reinekate salt (m 173-174o) and its dipicrate salt (m 201o, from H2O). [Norton et al. J Am Chem Soc 68 1330 1946, Mortimer Aust J Chem 11 84 1958, Augustine J Am Chem Soc 81 4667 1959, Beilstein 22 III/IV 3765.]

InChI:InChI=1/C6H14N2/c7-5-6-3-1-2-4-8-6/h6,8H,1-5,7H2

Synthetic route

(2-aminomethylpyridine) (3731-51-9) → C-piperidin-2-yl-methylamine (22990-77-8)

Conditions	Yield
With hydrogenchloride; hydrogen; platinum(IV) oxide In ethanol; water for 2.5h; Ambient temperature;	28.1%
With acetic acid; platinum Hydrogenation;
With hydrogen; Ra-Ni at 160 - 200℃; under 135014 - 150015 Torr; Product distribution / selectivity;
With hydrogen; Ni-Fe-6606 at 160℃; under 150015 Torr; Product distribution / selectivity;

(+-)-6-oxo-piperidine-2-carboxylic acid amide → C-piperidin-2-yl-methylamine (22990-77-8)

Conditions	Yield
With tetrahydrofuran; lithium aluminium tetrahydride

(+-)-<1-acetyl-<2>piperidyl>-acetone oxime → C-piperidin-2-yl-methylamine (22990-77-8)

Conditions	Yield
With hydrogenchloride; diethyl ether; phosphorus pentachloride

(+-)-N-<2>piperidylmethyl-acetamide → C-piperidin-2-yl-methylamine (22990-77-8)

Conditions	Yield
With hydrogenchloride

hydrogenchloride (7647-01-0) + (1-acetyl-[2]piperidyl)-acetone oxime + diethyl ether (60-29-7) + phosphorus pentachloride (10026-13-8, 874483-75-7) + water (7732-18-5) → C-piperidin-2-yl-methylamine (22990-77-8)

2-Cyanopyridine (100-70-9) → C-piperidin-2-yl-methylamine (22990-77-8)

Conditions	Yield
With ammonia; hydrogen; Ni-5584 In ethanol at 180℃; under 135014 Torr; for 6h; Product distribution / selectivity;

Upstream product

• 7647-01-0 hydrogenchloride 
• 60-29-7 diethyl ether 
• 10026-13-8 phosphorus pentachloride 
• 7732-18-5 water 
• 100-70-9 2-Cyanopyridine 
• 3731-51-9 2-(Aminomethyl)pyridine 

Downstream Products

• 78451-78-2 1,3-Dimethyl-4-phenyl-6,6a,7,8,9,10-hexahydro-1H-1,2,5,10a-tetraaza-benzo[e]azulene 
• 78451-73-7 4-(3-Chloro-phenyl)-1,3-dimethyl-6,6a,7,8,9,10-hexahydro-1H-1,2,5,10a-tetraaza-benzo[e]azulene 
• 54143-55-4 flecainide 
• 57415-44-8 flecainide hydrochloride 
• 1353131-52-8 ethyl (4-hydroxyphenyl)-1-[(1-oxido-hexahydro-[1,3,2]-diazaphospholo[1,5a]pyridine 1-yl)amino]acetate 
• 1353131-43-7 1-(4-chlorophenoxy)-hexahydro-[1,3,2]-diazaphospholo[1,5a]pyridine-1-oxide 
• 1353131-44-8 1-(4-nitrophenoxy)-hexahydro-[1,3,2]-diazaphospholo[1,5a]pyridine-1-oxide 
• 127722-73-0 N-<((2-piperidinyl)methyl)>benzamide 
• 4430-75-5 octahydro-1H-pyrido[1,2-a]pyrazine 
• 5015-92-9 3-Methyl-2-azachinolizidin 

Relevant articles and documents

Process for the preparation of 2-aminomethylpiperidine

The invention relates to a process for the preparation of aminomethylpyridines of the general formula (I) by hydrogenation of cyanopyridines of the general formula (II) with hydrogen under increased pressure optionally in the presence of a catalyst containing Ni, Fe or Co and optionally in the presence of ammonia.

Preparation of esters of phosphorus acids

Esters of phosphorus acids are prepared by an improved process whereby aromatic alcohols and phosphorus halides are reacted at specified temperatures in the presence of amine catalysts thereby providing high yields of substantially pure esters and allowing preparation of selected halogen-containing mono- and di-esters of phosphorus acids wherein halogen is directly bonded to phosphorus having substantially no side reactant contamination. The phosphorus esters are useful as intermediates in the preparation of plasticizers, oil additives and functional fluids.