Category: 130658-65-0

Application of 130658-65-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 130658-65-0, name is 1-(Pyridin-4-yl)piperidin-4-ol, molecular formula is C10H14N2O, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

EXAMPLE 31 Azodicarbonyldipiperidine (20.03 g), tributylphosphine (16.06 g) and 1-(4-pyridyl)-4-piperidin-1-ol (9.43 g) were added to a stirred solution of N-t-butyloxycarbonyl-4-aminophenol (11.08 g) in dry THF (300 ml), cooled under a blanket of nitrogen to 10 C. A thick precipitate formed and the mixture was stirred at ambient temperature for 20 hours during which time the mixture slowly thinned. The precipitated tributylphosphine oxide was removed by filtration and the residue concentrated in vacuo. The residue was purified by flash chromatography on silica gel using ethyl acetate followed by dichloromethane containing an increasing amount of methanol (up to 5% methanol) as eluent to give a solid (7.38 g). mp 192-195 C. A solution of this solid (4.22 g) in dichloromethane (400 ml) was treated with a saturated solution of hydrogen chloride in ether (50 ml) and the mixture was stirred for 64 hours. The mixture concentrated in vacuo and the residue crystallized from methanol/ether to give 1-(4-pyridyl)-4-(4-aminophenyloxy)piperidine hydrochloride (2.85 g), mp. 289-291 C. NMR: 1.73 (m,2H), 2.06 (m,2H), 3.64 (m,2H), 3.94(m,2H), 4.76 (m,1H), 7.12(d,2H), 7.24(d,2H), 7.34(d,2H), 8.23(d,2H), 10.32 (broad, 2H); MS: m/z 270 (MH)+. This solid (1.5 g) was dissolved in water (10 ml) and 2M sodium hydroxide added until precipitation was complete.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 130658-65-0, 1-(Pyridin-4-yl)piperidin-4-ol.

Reference:
Patent; Zeneca Limited; US6313127; (2001); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 130658-65-0 ,Some common heterocyclic compound, 130658-65-0, molecular formula is C10H14N2O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

The 3-[1-(4-pyridyl)piperidin-4-yloxy]aniline used as a starting material was prepared as follows:- Diethyl azodicarboxylate (3 ml) was added over 15 minutes to a stirred mixture of 1-(4-pyridyl)piperidin-4-ol (3.39 g), 3-(N-tert-butoxycarbonylamino)phenol (Chemical Abstracts, vol. 119, abstract 139113; PCT Patent Application WO 9306085; 3.98 g), triphenylphosphine (4.99 g) and THF (150 ml) which had been cooled to 4 C. The resultant mixture was stirred for 48 hours at ambient temperature. The solvent was evaporated and the residue was purified by column chromatography using a 9:1 mixture of methylene chloride and methanol as eluent. The resultant foam was crystallized from diethyl ether to give tert-butyl N-{3-[1-(4-pyridyl)piperidin-4-yloxy]phenyl}carbamate (4.65 g), m.p. 165-166 C. A 2.2M solution of hydrogen chloride in methanol (45 ml) was added over 15 minutes to a stirred solution in methanol (25 ml) of a portion (2.53 g) of the carbamate so obtained. The mixture was stirred at ambient temperature for 24 hours. The solvent was evaporated and the residue was dissolved in water (50 ml). A 1M aqueous sodium hydroxide solution (25 ml) was added and the mixture was stirred for 1 hour. The precipitate was collected, washed with water and with diethyl ether and dried. There was thus obtained 3-[1-(4-pyridyl)piperidin-4-yloxy]aniline (1.71 g), m.p. 184-186 C.; NMR Spectrum 1.60 (m, 2H), 1.96 (m, 2H), 3.23 (m, 2H+H2O), 3.65 (m, 2H) 4.48 (m, 1H), 5.00 (s, 2H), 6.16 (m, 3H), 6.82 (d, 2H), 6.88 (t, 1H), 8.15 (d, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,130658-65-0, its application will become more common.

Reference:
Patent; ZENECA LIMITED; US2003/207882; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem