58547-68-5

Usage

Uses

Used in Pharmaceutical Industry:
Piperidine, 1-(4-hydroxybenzoyl)is used as a reactant for the preparation of (phenoxyalkyl)imidazoles, which are potent H3-receptor histamine antagonists. These antagonists play a crucial role in the treatment of various medical conditions, such as allergies, asthma, and other inflammatory diseases, by blocking the action of histamine, a substance involved in immune responses and inflammation.
In the synthesis of these imidazoles, Piperidine, 1-(4-hydroxybenzoyl)serves as a key building block, providing the necessary structural elements for the formation of the final product. Its reactivity and compatibility with various synthetic routes make it an ideal candidate for the development of new and improved H3-receptor histamine antagonists, potentially leading to more effective treatments for a range of medical conditions.

Upstream product

• 110-89-4 piperidine 
• 38597-39-6 4-nitrophenyl 4-hydroxybenzoate 
• 120-47-8 Ethyl 4-hydroxybenzoate 
• 402-45-9 4-hydroxybenzotrifluoride 
• 2591-86-8 N-Formylpiperidine 
• 99-96-7 4-hydroxy-benzoic acid 
• 623-05-2 (4-hydroxyphenyl)methanol 
• 123-08-0 4-hydroxy-benzaldehyde 
• 27914-73-4 4-acetoxybenzoyl chloride 
• 2345-34-8 4-acetyloxy-benzoic acid 
• 60397-69-5 Acetic acid 4-(piperidine-1-carbonyl)-phenyl ester 

Downstream Products

• 925438-96-6 piperidin-1-yl-(4-{3-[4-(1-trityl-1H-imidazol-4-ylmethyl)-piperidin-1-yl]-propoxy}-phenyl)-methanone 
• 210961-92-5 4-(piperidine-1-carbonyl)benzoic acid 
• 73152-41-7 4-(piperidin-1-ylmethyl)phenol 

Relevant academic research and scientific papers

FLUORINE-CONTAINING COMPOUND AND ANTI-CANCER MEDICAL USE THEREOF

The present invention provides a fluorine-containing compound shown in Formula II/III and its anti-cancer medical use.

Organophotoredox-Mediated Amide Synthesis by Coupling Alcohol and Amine through Aerobic Oxidation of Alcohol

The combination of an organic photocatalyst [4CzIPN (1,2,3,5-tetrakis(carbazol-9-yl)-4,6 dicyanobenzene) or 5MeOCzBN (2,3,4,5,6-pentakis(3,6-dimethoxy-9 H-carbazol-9-yl)benzonitrile)], quinuclidine, and tetra-n-butylammonium phosphate (hydrogen-bonding catalyst) was employed for amide bond formations. The hydrogen-bonded OH group activated the adjacent C?H bond of alcohols towards hydrogen atom transfer (HAT) by a radical species. The quinuclidinium radical cation, generated through single-electron oxidation of quinuclidine by the photocatalyst, employed to abstract a hydrogen atom from the α-C?H bond of alcohols selectively due to a polarity effect-produced α-hydroxyalkyl radical, which subsequently converted to the corresponding aldehyde under aerobic conditions. Then the coupling of the aldehyde and an amine formed a hemiaminal intermediate that upon photocatalytic oxidation produced the amide.

Metal–Organic Framework Based on Copper and Carboxylate-Imidazole as Robust and Effective Catalyst in the Oxidative Amidation of Carboxylic Acids and Formamides

A metal–organic framework (MOF) based on copper and 1,3-bis(carboxymethyl)imidazole (bcmim) was prepared on a gram scale by using a precipitation method at room temperature. The Cu(bcmim)2MOF was shown to be an efficient catalyst for the preparation of amides through an oxidative coupling between carboxylic acids and formamides in the presence of an oxidant, such as tert-butyl hydroperoxide (TBHP). The method for the preparation of the amides is robust regardless of the carboxylic acid and gives good conversions with good selectivity. The heterogeneous catalyst was recovered unaltered after the reaction, was easily separated from the reaction mixture, and subsequently reactivated by suitable treatment. Moreover, the coupling reaction was scaled up to a gram scale, which allowed for the preparation of valuable products, such as fatty acid amides (i.e., 1-palmitoylpiperidine).

Zn(OTf)2-promoted chemoselective esterification of hydroxyl group bearing carboxylic acids

Selective esterification of aliphatic and aromatic carboxylic acids with various alcohols is studied using triphenylphosphine, I2, and a catalytic amount of Zn(OTf)2. Use of this catalyst allows the formation of esters at a faster rate with good to excellent yield by activating the in situ generated acyloxyphosphonium ion intermediate. During the esterification process, both their aromatic and aliphatic hydroxyl groups are fully preserved from transesterification. The results show that the bulkiness and the reactivity of this doubly activated intermediate III control the selectivity and the rate of the reaction, respectively. The method is also useful for direct amidation reactions.

Synthesis of tertiary amides from anionically activated aromatic trifluoromethyl groups

Figure presented In this paper, a novel synthesis of tertiary amides from anionically activated aromatic trifluoromethyl groups is presented. Anionically activated trifluoromethyl groups react with secondary amines under aqueous conditions to afford tertiary amides. The mechanism involves initial elimination of hydrogen fluoride by an E1cB mechanism to afford an electrophilic quinone methide- or azafulvene-type intermediate that reacts with secondary amines under aqueous conditions to afford the tertiary amide in good yield (up to 99%).

Structure-reactivity correlations in nucleophilic substitution reactions of Y-substituted phenyl X-substituted benzoates with anionic and neutral nucleophiles

A kinetic study is reported for the reactions of 4-nitrophenyl X-substituted benzoates (1a-l) and Y-substituted phenyl benzoates (2a-l) with two anionic nucleophiles (OH- and CN-) and three amines (piperidine, hydrazine, and glycylglycine) in 80 mol% H2O-20 mol% dimethyl sulfoxide (DMSO) at 25.0 ± 0.1 °C. Each Hammett plot exhibits two intersecting straight lines for the reactions of 1a-l with the anionic nucleophiles and piperidine, while the Yukawa-Tsuno plots for the same reactions are linear. The Hammett plots for the reactions of 2a-l with hydrazine and glycylglycine demonstrate much better linear correlations with σ- constants than with σ° or σ constants, indicating that the leaving group departure occurs at the rate determining step (RDS). On the contrary, σ- constants result in poorer Hammett correlation than σ° constants for the corresponding reactions with OH- and CN-, indicating that the leaving group departure occurs after the RDS for the reactions with the anionic nucleophiles. The large ρX value (1.7 ± 0.1) obtained for the reactions of 1a-l with the anionic nucleophiles supports the proposal that the reactions proceed through an addition intermediate with its formation being the RDS. The Royal Society of Chemistry 2006.

Reduction of CYP450 inhibition in the 4-[(1H-imidazol-4-yl)methyl] piperidine series of histamine H3 receptor antagonists

A novel series of histamine H3 receptor antagonists based on the 4-[(1H-imidazol-4-yl)methyl]piperidine template displaying low CYP2D6 and CYP3A4 inhibitory profiles has been identified. Structural features responsible for the reduction of P450 activity, a typical liability of 4-substituted imidazoles, have been established.

2-CYANOPYRROLOPYRIMIDINES AND PHARMACEUTICAL USES THEREOF

The invention relates to pyrrolo pyrimidines of formula (I), wherein Y represents -(CH2)t-O- or -(CH2)r-S-, p is 1 or 2, r is 1, 2 or 3, t is 1, 2 or 3, or Y is -(CH2)j- or -CH=CH-, j is 1 or 2; p is 1 or 2, or Y is -(CH2)f-, f is 1 or 2, p is 1, and the further radicals and symbols have the meaning as defined herein; their preparation, their use as pharmaceuticals, pharmaceutical compositions containing them, the use of such a compound for the manufacture of a pharmaceutical preparation for the treatment of neuropathic pain and to a method for the treatment of such a disease in animals, especially in humans.

A novel series of (phenoxyalkyl)imidazoles as potent H3-receptor histamine antagonists

[[(4-Nitrophenyl)X]alkyl]imidazole isosteres (where X = NH, S, CH2S, O) of previously described [[(5-nitropyrid-2-yl)X]ethyl]imidazoles (where X = NH, S) have been synthesized and evaluated for H3-receptor histamine antagonism in vitro (K(i) for [3H]histamine release from rat cerebral cortex synaptosomes) and in vivo (ED50 per os in mice on brain tele- methylhistamine levels). Encouraging results led to the synthesis and testing of a novel series of substituted (phenoxyethyl)- and (phenoxypropyl)imidazoles. From the latter, 4-[3-(4-cyanophenoxy)propyl]-1H- imidazole (10a, UCL 1390; K(i) = 12 nM, ED50 = 0.54 mg/kg) and 4-[3-[4- (trifluoromethyl)-phenoxy]propyl]-1H-imidazole (10c, UCL 1409; K(i) = 14 nM, ED50 = 0.60 mg/kg) have been selected as potential candidates for drug development. For 16 [(aryloxy)ethyl]imidazoles the relationship between in vitro and in vivo potency is described by the equation log ED50 = 0.47 log K(i) + 0.20 (r = 0.78).