ChemicalBook CAS DataBase List 4-Aminotetrahydropyran hydrochloride

4-Aminotetrahydropyran hydrochloride synthesis

5synthesis methods

Product Name:4-Aminotetrahydropyran hydrochloride
CAS Number:33024-60-1
Molecular formula:C5H12ClNO
Molecular Weight:137.61

A mixture of 4-(hydroxyimino)-3,5,6-trihydro-2H-pyran (43.4 mmol) and Raney Nickel (200 mg) in ethanol was hydrogenated (90 psi) at room temperature for 3 days. The mixture was filtered through a pad of Celite, washed with MeOH, and concentrated. The residue was dissolved in MeOH, treated with HCl (4 N in dioxane, 60 mmol), and concentrated to give perhydro-2H-pyran-4-ylamine hydrochloride (4-Aminotetrahydropyran hydrochloride).

29943-42-8 Synthesis

29943-42-8
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33024-60-1
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Yield:-

Reaction Conditions:

with ammonium formate;palladium 10% on activated carbon in methanol;water at 20;

Steps:

17
Reference Example 17 Tetrahydro-2H-pyran-4-ylamine hydrochloride To a solution of tetrahydro-4H-pyran-4-one (4.30 g, 43.0 mmol) in methanol (112 ml) was added an aqueous solution (12.5 ml) of ammonium formate (25 g, 400 mmol). Insolubles were completely dissolved and then 10% palladium carbon (5.1 g) was added thereto, which was stirred at room temperature overnight. After the insolubles were filtrated off to obtain a filtrate, which was concentrated, and to the residue was added ethanol (100 ml) and concentrated hydrochloric acid (7.5 ml). The solvent was distilled off under reduced pressure to give an objective product, which was collected by filtration and washed with ether. ¹H-NMR (DMSO-d₆) δ: 1.54-1.74 (2H, m), 1.82-1.98 (2H, m), 3.27-3.38 (3H, m), 3.87-3.94 (2H, m), 9.05 (3H, bs). IR (KBr) cm^-1; 2966, 1377, 1163, 1088, 1015, 986, 862.

References:

Takeda Pharmaceutical Company Limited EP1535922, 2005, A1 Location in patent:Page/Page column 40

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