18903-01-0

Basic information

• Product Name: TRANS-1-CINNAMYLPIPERAZINE
• Synonyms: 1-TRANS-CINNAMYL PIPERAZINE;1-((E)-3-PHENYLALLYL)PIPERAZINE;1-(CINNAMYL)PIPERAZINE;1-(3-PHENYL-ALLYL)-PIPERAZINE;LABOTEST-BB LT00233225;N-CINNAMYLPIPERAZINE;TIMTEC-BB SBB000411;1-(3-Phenyl-2-Propenyl)Piperazine
• CAS NO: 18903-01-0
• Molecular Formula: C₁₃H₁₈N₂
• Molecular Weight: 202.3
• EINECS: 242-652-0
• Product Categories: Pharmaceutical Intermediates;Piperidines, Piperidones, Piperazines
• Mol File: 18903-01-0.mol

Chemical Properties

• Melting Point: 39-44 °C(lit.)
• Boiling Point: 129 °C1 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: clear colorless to yellow liquid after melting
• Density: 0.989 g/mL at 25 °C(lit.)
• Vapor Pressure: 7.92E-05mmHg at 25°C
• Refractive Index: 1.574-1.576
• PKA: 9.17±0.10(Predicted)
• CAS DataBase Reference: TRANS-1-CINNAMYLPIPERAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-1-CINNAMYLPIPERAZINE(18903-01-0)
• EPA Substance Registry System: TRANS-1-CINNAMYLPIPERAZINE(18903-01-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 18903-01-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
TRANS-1-CINNAMYLPIPERAZINE is used as a building block and metabolite for the development of Flunarizine (F455200), a selective calcium entry blocker. This application is for the prophylaxis of severe refractory migraine and symptomatic treatment of vestibular vertigo, as it helps in managing the symptoms and preventing the occurrence of these conditions.
Used in Chemical Synthesis:
TRANS-1-CINNAMYLPIPERAZINE is used as a building block for synthesizing Incentrom A derivatives. This application is for creating new compounds with potential applications in various fields, including pharmaceuticals, materials science, and other industries.
Used in Antiprotozoal Research:
TRANS-1-CINNAMYLPIPERAZINE is used as a test compound for investigating its in vitro efficacy as an antiprotozoal agent against Philasterides dicentrarchi. This application is for understanding the compound's potential to combat protozoan infections and contribute to the development of new antiprotozoal treatments.

InChI:InChI=1/C13H18N2/c1-2-5-13(6-3-1)7-4-10-15-11-8-14-9-12-15/h1-7,14H,8-12H2/p+2/b7-4+

Upstream product

• 289491-31-2 1-benzoyl-4-(3-phenyl-allyl)-piperazine 
• 2687-12-9 cinnamyl chloride 
• 110-85-0 piperazine 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 163596-56-3 C₁₃H₁₈N₂*ClH 
• 104-54-1 3-Phenylpropenol 
• 117109-07-6 1-(3-Phenyl-2-propenyl)-4-formylpiperazine 
• 105041-05-2 3-phenyl-2-propenoyl bromide 
• 4392-24-9 Cinnamyl bromide 
• 82387-46-0 1-Cinnamyl-4-(ethoxycarbonyl)piperazine 
• 82387-46-0 ethyl <4-(3-phenyl-2-propenyl)-1-piperazinyl> carboxylate 

Downstream Products

• 89513-70-2 6,6-Dimethyl-4-[4-((E)-3-phenyl-allyl)-piperazin-1-yl]-6,7-dihydro-5H,10H-9-thia-1,3,10-triaza-anthracen-8-one 
• 103378-69-4 N-(5H-Dibenzo[a,d]cyclohepten-5-yl)-4-[4-((E)-3-phenyl-allyl)-piperazin-1-yl]-butyramide 
• 132019-61-5 N-(5,11-Dihydro-10-thia-dibenzo[a,d]cyclohepten-5-yl)-4-[4-((E)-3-phenyl-allyl)-piperazin-1-yl]-butyramide 
• 112063-62-4 N-(4aS,5S,11aS)-1,2,3,4,4a,5,11,11a-Octahydro-10-thia-dibenzo[a,d]cyclohepten-5-yl-4-[4-((E)-3-phenyl-allyl)-piperazin-1-yl]-butyramide 
• 85630-73-5 N-{2-Chloro-5-methoxy-4-[4-((E)-3-phenyl-allyl)-piperazine-1-carbonyl]-phenyl}-2-(4-chloro-phenoxy)-acetamide 
• 110629-30-6 (2,6-Dimethyl-3-nitro-pyridin-4-yl)-{2-[4-((E)-3-phenyl-allyl)-piperazin-1-yl]-ethyl}-amine; hydrochloride 
• 177214-91-4 3-Methyl-4-{3-[4-(3-phenyl-2-propen-1-yl)piperazin-1-yl]propylthio}2-[(2-pyridinylthio)methyl]pyridine hydrochloride salt 

Relevant articles and documents

Design and synthesis of new potent N,N-bis(arylalkyl)piperazine derivatives as multidrug resistance (MDR) reversing agents

A series of 1,4-substituted arylalkyl piperazine derivatives were synthesized and studied with the aim to obtain potent P-gp-dependent multidrug-resistant (MDR) reversers. The new compounds were designed on the basis of the structures of our previous arylamine ester derivatives endowed with high P-gp-dependent multidrug resistance reversing activity. All new compounds were active in the pirarubicin uptake assay on the doxorubicin–resistant erythroleukemia K562 cells (K562/DOX). In particular, compounds bearing methoxy aromatic moieties showed fairly high reversal activities. The most potent compounds, 8, 9, 10 and 13, were further studied by evaluating their doxorubicin cytotoxicity enhancement (reversal fold, RF) and the inhibition of P-gp-mediated rhodamine-123 (Rhd 123) efflux on the K562/DOX cell line. The results of all pharmacological assays indicated that the combination of a basic piperazine scaffold with arylalkyl residues allowed us to obtain very interesting P-gp modulating compounds. Two long-lasting P-gp pump modulators (9 and 10) were identified; they were able to inhibit remarkably the P-gp substrate rhodamine-123 efflux on the resistant K562/DOX cell line after 60 min. Overall compound 9 appeared the most promising compound being a potent and long-lasting P-gp–dependent MDR modulator.

A Simple, Broad-Scope Nickel(0) Precatalyst System for the Direct Amination of Allyl Alcohols

The preparation of allylic amines is traditionally accomplished by reactions of amines with reactive electrophiles, such as allylic halides, sulfonates, or oxyphosphonium species; such methods involve hazardous reagents, generate stoichiometric waste streams, and often suffer from side reactions (such as overalkylation). We report here the first broad-scope nickel-catalysed direct amination of allyl alcohols: An inexpensive NiII/Zn couple enables the allylation of primary, secondary, and electron-deficient amines without the need for glove-box techniques. Under mild conditions, primary and secondary aliphatic amines react smoothly with a range of allyl alcohols, giving secondary and tertiary amines efficiently. This “totally catalytic” method can also be applied to electron-deficient nitrogen nucleophiles; the practicality of the process was demonstrated in an efficient, gram-scale preparation of the calcium antagonist drug substance flunarizine (Sibelium).

Synthesis method of cinnamyl piperazine

The invention discloses a synthesis method of cinnamyl piperazine. The method includes the steps of: a) adding a solvent into a reaction kettle and adding piperazine to uniformly dissolve the piperazine, dropwisely adding hydrochloric acid at 20-25 DEG C until the pH of the reaction solution is 2, which is the terminal, and after the reaction is performed for 1 h, cooling the reaction solution to 20 DEG C, and centrifugally spin-filtering the reaction solution to obtain piperazine dihydrochloride; b) adding the solvent into the reaction kettle, adding the piperazine dihydrochloride and the piperazine with stirring at the same time, and performing a reaction at 68-85 DEG C for 0.5-3 h; c) reducing the temperature to 45-55 DEG C, dropwisely adding cinnamyl chloride, and then increasing the temperature to 60-75 DEG C to perform a temperature maintained reaction for 1-4 h, and reducing the temperature to 10-35 DEG C, performing centrifugal separation, sucking a mother liquid into a distillation reaction kettle, heating the distillation mother liquid to recycle the solvent, adding pure water, and dropwisely adding an alkali liquid to regulate the pH to 9-12, and adding chloroform to perform extraction, drying the mixture, and evaporate-drying the chloroform to obtain the cinnamyl piperazine. The synthesis method reduces production steps and pollutant emission, and is more suitable for modern industrial production.

Design, synthesis and in vitro activity of 1,4-disubstituted piperazines and piperidines as triple reuptake inhibitors

Monoamine transporters regulate the concentration of monoamine neurotransmitters, which are essential for vital physiological processes, and their dysfunction can cause several central nervous system diseases. Monoamine transporters currently appear to be the potential target in the management of these disorders. In this study, homologation and bioisosterism techniques have been used in the designing of new 1,4-disubstituted piperazines and piperidines. These derivatives were synthesized and evaluated as potential triple reuptake inhibitors for studying the structure-activity relationships. The most advanced compound, 1-(4-(5-benzhydryl-1H-tetrazol-1-yl)butyl)-4-(3-phenylpropyl)piperazine (2i), was able to inhibit monoamine neurotransmitter reuptake in an in vitro test (IC50?=?158.7?nM for 5-HT, 99?nM for NE and 97.5?nM for DA). These novel potent triple reuptake inhibitor-based 1,4-disubstituted piperazine and piperidine scaffolds deserve further systematic optimization and pharmacological evaluation.

Unique spirocyclopiperazinium salt I: Synthesis and structure-activity relationship of spirocyclopiperazinium salts as analgesics

Based on the structure of compound 3, two series of spirocyclopiperazinium derivatives 7a-n and 10a-h were synthesized and evaluated for their in vivo analgesic and sedative activities. Compounds 7f and 10c were discovered to exhibit excellent analgesic activity. Structure-activity relationships revealed that anion of the quaternary salt affected the analgesic and sedative activity significantly; the allyl group is a most effective group among the compounds 7a-n; the electron-released substitute on the aromatic ring is favorable to increase the analgesic activity.

Synthesis and pharmacological study of new calcium antagonists analogues of cinnarizine and flunarizine

Several phosphonic diethyl esters were synthesized and their calcium antagonistic activity evaluated in vitro.The diethyl phosphonate group was condensed on substituted , , , , and groups.Despite the presence of the diethyl phosphonate moiety and the benzhydrylpiperazinyl group, both present in potent calcium antagonist structures, only 1 of the 19 synthesis compounds exhibited a calcium antagonistic profile. diethyl phosphonate / benzhydryl piperazine / calcium antagonist

Saturated heterocyclic carboxamide derivatives

A saturated heterocyclic carboxamide derivative of the following general formula (I) and salts thereof which have platelet activating factor (PAF) antagonizing activity. STR1

Adamantane-piperazine derivatives

Adamantane derivatives of this invention are represented by the formula STR1 wherein R1 is STR2 or --CH2 -- and R2 is STR3 or --CH2 CH=CH--. Said derivatives are cerebral vasodilators or intermediates for the same.