- Preparation method of alpha, alpha-diphenyl-4-piperidine methanol
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The invention discloses a preparation method of alpha, alpha-diphenyl-4-piperidine methanol, which comprises the following steps of by using benzophenone and 4-cyanopyridine as raw materials, carrying out free radical coupling reaction under the action of alkali metal to obtain alpha, alpha-diphenyl-4-piperidine methanol, reacting the obtained alpha, alpha-diphenyl-4-pyridine methanol with a benzylation reagent to generate N-benzyl-alpha, alpha-diphenyl-4-pyridine methanol, carrying out hydroboration reduction on the N-benzyl-alpha, alpha-diphenyl-4-pyridine methanol to obtain (1-benzyl-1, 2, 3, 6-tetrahydropyridine-4-yl)benzhydrol, ane enabling (1-benzyl-1, 2, 3, 6-tetrahydropyridine-4-yl)benzhydrol to be subjected to catalytic hydrogenation and debenzylation protection to obtain alpha, alpha-diphenyl-4-piperidine methanol. The method has the advantages of cheap and accessible raw materials, high reaction yield and high controllability, and is suitable for industrial production requirements.
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- Design and synthesis of antimicrobial active new molecular entities of N-substituted pipradol derivatives
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Synthesis of antimicrobial 4-(hydroxyldiphenyl methyl)piperidin-1-yl)(substituted phenyl)methanone derivatives by using conventional chemical reactions to produces feasible and entirely new chemical entities (NCE’S) which were having a great potential microbial activities equivalent to fexofenidine used as a biological standard. This invention may help full for derive more potential pipradol molecules with peptide bond linkage.
- Sri Ramudu,Ramachandran,Venkat Rao,Murali Krishna,Satya Narayana,Reddy, Kallam Naveen
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p. 2113 - 2115
(2017/10/06)
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- A α, α-diphenyl-4-piperidine methanol synthesis method
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The invention discloses a method for synthesis of alpha,alpha-diphenyl-4-piperidine methanol. The method comprises the steps: taking 4-piperidine formic acid as a raw material, carrying out a reaction with an acetylation reagent to obtain N-acetyl piperidine formic acid; firstly generating N-acetyl piperidine formyl chloride from the obtained N-acetyl piperidine formic acid, and then carrying out a Friedel-Crafts acylation reaction with benzene to generate N-acetyl-4-benzoyl piperidine; carrying out a Grignard reaction of the obtained N-acetyl-4-benzoyl piperidine with phenyl magnesium halide to obtain N-acetyl-alpha,alpha-diphenyl-4-piperidine methanol; and deacetylating the N-acetyl-alpha,alpha-diphenyl-4-piperidine methanol to obtain the alpha,alpha-diphenyl-4-piperidine methanol. The synthesis method has the characteristics of cheap and easily obtained raw materials, simple process steps, high reaction yield and low costs of raw materials, and is suitable for industrialized production.
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- Synthesis and in vitro antiproliferative activity of diphenyl(sulphonylpiperidin-4-yl)methanol derivatives
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A series of novel diphenyl(piperidin-4-yl)methanol derivatives 10(a-n) were synthesized and characterized by 1H NMR, LC/MS, FTIR, and elemental analyses. All the synthesized compounds were evaluated for cell proliferation by MTT assay. The antiproliferative effects of the synthesized compounds were tested against viable human skin fibroblast cell line and carcinoma cell lines, namely HeLa cells, HT-29 cells, MCF-7 cells, and HepG-2 cells in comparing the positive and negative control. Among the synthesized compounds, (10b) and (10g) have been identified as potent antiproliferative agents.
- Benaka Prasad,Vinaya,Ananda Kumar,Swarup, Sanjay,Rangappa
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p. 220 - 235
(2011/01/12)
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- Synthesis of terfenadine carboxylate
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A synthesis of terfenadine carboxylate, 1, a metabolite of terfenadine 2, is described. In the key step, the sodium salt of 2-(4-bromo-phenyl)-2-methylpropionic acid, 7, was lithiated via a metal-halogen exchange using t-BuLi and subsequently condensed with 4-[4-(hydroxydiphenylmethylpiperidin-1-yl]butyraldehyde, 5, to afford terfenadine carboxylate, 1.
- Patel, Sunil,Waykole, Liladhar,Repic, Oljan,Chen, Kau-Ming
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p. 4699 - 4710
(2007/10/03)
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- Synthesis of α,α-diphenyl-4-piperidine-methanol (azacyclonol), an intermediate for terfenadine
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Starting from diphenyl 4-pyridylcarbinol (2), synthesis of azacyclonol (7) has been carried out by a series of reactions involving quarternisation, borohydride reduction, catalytic transfer hydrogenation and N-demethylation.
- Sathe, Dhananjay G.,Kulkarni, Pravin B.,Kulkarni, Vithal M.
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p. 475 - 476
(2007/10/02)
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- 4-[(diaryl)hydromethyl]-1-piperidinealkanols and esters and carbamates thereof useful in the treatment of allergic disorders
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Novel compounds of the formula: STR1 are disclosed wherein Ar and Ar1 are phenyl, sustituted phenyl or pyridinyl, "alk" is a C1 -C12 straight or branched hydrocarbon chain, and R is H, loweralkylcarbonyl, arylcarbonyl, or aminocarbonyl where the amino is unsubstituted or substituted by one or two groups selected from loweralkyl or aryl. The compounds of this invention are useful in the treatment of allergic disorders.
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- 4-[diaryl)hydroxymethyl]-1-piperidinealkylcarboxylic acids, salts and esters useful in the treatment of allergic disorders
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Novel compounds useful in the treatment of allergic disorders and having the formula: STR1 where Ar and Ar1 are pyridinyl, phenyl, or substituted phenyl and where Y is --OH,--O? M≈ m,--O--loweralkyl, --O--Aryl, or NR1 R2 (R1, R2 =H, loweralkyl, aryl) are herein disclosed.
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- Arylalkylheterocyclic amines,N-substituted by aryloxyalkyl group in a method for allergy treatment
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A method of inhibiting Type 1 allergic responses in a living animal body with substituted heterocyclic amines is disclosed wherein the active agents are expressed generally by the formula which includes certain known and certain known compounds: STR1 wherein P is zero, one or two; m is one to six inclusive; A is selected from hydrogen, hydroxy or cyano; d is zero or one; Q is --CH--, CH2 -- or STR2 n is zero or one and when Q is --CH-- and n is one, a double bond is formed with one of the adjacent carbons but not both at the same time, and when n and d are zero at the same time, a double bond is formed between the α carbon and a carbon of the central heterocyclic amine ring; Ar, D and R are selected from phenyl, substituted phenyl, pyridinyl, thienyl, furanyl or naphthyl and in addition, R may have the values benzyl, substituted benzyl, cycloalkyl or loweralkyl and D may additionally have the values: 2H-1-benzopyran-2-one,4-oxo-4H-1-benzopyran-2-carboxylic acid loweralkyl ester, 2,3-dihydro-4H-1-benzopyran-4-one, 1,4-benzodioxanloweralkyl-2-yl or 1,1'-biphenyl-4-yl and the pharmaceutically acceptable salts thereof.
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- Synthesis and Antiallergy Activity of 4-(Diarylhydroxymethyl)-1-piperidines and Structurally Related Compounds
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A series of 4-(diarylhydroxymethyl)-1-piperidines was synthesized and evaluated for antiallergy activity.Several analogues had potent activity in the passive foot anaphylaxis (PFA) assay, an IgE-mediated model useful in the detection of compounds possessing antiallergic activity.In particular 1--1-piperidinyl>propoxy>-3-methoxyphenyl>ethanone (1, AHR-5333) was more potent than oxatomide and terfenadine in this assay.
- Walsh, David A.,Franzyshen, Stephen K.,Yanni, John M.
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p. 105 - 118
(2007/10/02)
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- 4-[(α,α-diaryl)-hydroxymethyl]-1-piperidinylalkyl-cyclic carbamate derivatives as allergic response inhibitors
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4-[(α,α-Diaryl)-hydroxymethyl]-1-piperidinylalkylcyclic carbamate derivatives having the formula: STR1 wherein; R is hydrogen, loweralkyl, cycloalkyl, phenyl and substituted phenyl; Ar and Ar1 are phenyl, substituted phenyl or pyridinyl; alk is a straight or branched hydrocarbon chain; R1 is loweralkyl substituted for hydrogen on a ring carbon. The compounds are useful antihistamines and in controlling allergic response.
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