4734-09-2

Basic information

• Product Name: 4-(2-METHYLPROPOXY)-BENZENEMETHANAMINE
• Synonyms: 4-(2-METHYLPROPOXY)-BENZENEMETHANAMINE;BENZENEMETHANAMINE, 4-(2-METHYLPROPOXY)-;UKRORGSYN-BB BBV-032489;4-Isobutoxybenzylamine;p-Isobutoxybenzylamine;4-(2-METHYLPROPOXY)-BENZENEMETHAMINE;(4-isobutoxyphenyl)methanamine;[4-(2-methylpropoxy)phenyl]methanamine
• CAS NO: 4734-09-2
• Molecular Formula: C₁₁H₁₇NO
• Molecular Weight: 179.26
• EINECS: 1592732-453-0
• Mol File: 4734-09-2.mol

Chemical Properties

• Boiling Point: 276.6±15.0 °C(Predicted)
• Flash Point: 116.4±13.6 oC, Calc.*
• Appearance: /
• Density: 0.977±0.06 g/cm3 (20 oC 760 Torr), Calc.*
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 9.30±0.10(Predicted)
• CAS DataBase Reference: 4-(2-METHYLPROPOXY)-BENZENEMETHANAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2-METHYLPROPOXY)-BENZENEMETHANAMINE(4734-09-2)
• EPA Substance Registry System: 4-(2-METHYLPROPOXY)-BENZENEMETHANAMINE(4734-09-2)

Safety Data

• Hazardous Substances Data: 4734-09-2(Hazardous Substances Data)

Upstream product

• 882035-15-6 4-isobutyloxybenzaldehyde oxime 
• 123-08-0 4-hydroxy-benzaldehyde 
• 18962-07-7 4-isobutoxybenzaldehyde 
• 5203-15-6 4-(2-methylpropoxy)benzonitrile 
• 767-00-0 4-cyanophenol 
• 1194-02-1 4-fluorobenzonitrile 
• 459-57-4 4-fluorobenzaldehyde 
• 1030513-44-0 4-isobutoxybenzamide 
• 50690-54-5 2-[4-(2-methylpropoxy)phenyl]acetonitrile 
• 99-96-7 4-hydroxy-benzoic acid 
• 99-76-3 methyl 4-hydroxylbenzoate 
• 124403-90-3 methyl 4-(2-methylpropoxy)benzoate 
• 30762-00-6 4-isobutoxybenzoic acid 
• 156-38-7 4-hydroxyphenylacetate 

Downstream Products

• 706779-91-1 N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide 
• 639863-75-5 1-(isocyanatomethyl)-4-(2-methylpropoxy)benzene 
• 639863-77-7 1-(4-fluorobenzyl)-3-(4-isobutoxybenzyl)-1-(piperidin-4-yl)urea 
• 1080491-31-1 N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N’-(4-(2-methylpropyloxy)phenylmethyl)carbamide tartaric acid 
• 955997-87-2 N,N'-bis(4-isobutoxybenzyl)urea 
• 1388858-78-3 N-(4-isobutoxybenzyl)-N'-(4-fluorobenzyl)urea 
• 706782-28-7 Pimavanserin tartrate 

Relevant articles and documents

Application of pimavanserin in preparation of antitumor drugs

The invention relates to application of pimavanserin in preparation of antitumor drugs, belongs to the technical field of medicines, and particularly relates to novel application of pimavanserin in preparation of antitumor drugs. The structural formula of the pimavanserin is shown in the formula I. The biological activity test of the compound shows that the compound has antitumor activity and is a novel antitumor drug.

PROCESS FOR THE PREPARATION OF A PHARMACEUTICAL AGENT

This invention relates to a process for the preparation of pimavanserin comprising: (i) providing an acid addition salt of pimavanserin; (ii) dissolving the acid addition salt of pimavanserin in an aqueous solvent to form an aqueous solution; (ill) washing the aqueous solution obtained in step (ii) with an organic solvent; and (iv) adding a base to the washed aqueous solution to form pimavanserin. The invention also relates to a process for the preparation of an acid addition salt of pimavanserin additionally comprising step (v) of converting pimavanserin into an acid addition salt of pimavanserin. The invention also relates to pimavanserin or an acid addition salt thereof obtainable by the process, and to the use of pimavanserin hydrochloride, pimavanserin hydrogen sulfate or pimavanserin acetate for preparing pimavanserin or an acid addition salt thereof.

Method for synthesizing P-isobutoxybenzylamine

The invention provides a method for synthesizing p-isobutoxy benzylamine. P-hydroxybenzyl alcohol is used as a raw material; the method comprises the following steps: reacting p-hydroxybenzyl alcoholwith halogenated isobutane to obtain p-isobutoxy benzyl alcohol; according to the method, p-isobutoxybenzylamine is obtained by taking p-isobutoxybenzylamine as a raw material and performing a seriesof steps such as chlorination and ammonolysis, so the use of relatively harsh reduction conditions with certain risk is avoided, and the produced p-isobutoxybenzylamine is high in purity and excellentin quality and is an excellent route with industrial prospect.

PROCESS FOR THE MANUFACTURING OF PIMAVANSERIN

The present invention relates to a new process for manufacturing 1-(4-fluorobenzyl)-3-(4-iso-butoxyphenyl)-1-(1-methylpiperidin-4-yl)urea, with the INN name pimavanserin, and its hemitartrate salt.

An improved process for the preparation of pimavanserin tartrate

A practical synthetic route to pimavanserin tartrate, in which the target compound was obtained with 99.84% purity and in 46% total yield via a 5-step synthesis starting from 4-hydroxybenzaldehyde and (4-fluorophenyl)methanamine, is reported. The main advantages of the route include inexpensive starting materials, mild reaction conditions and an acceptable overall yield.

Synthetic method of Pimavanserin

The invention belongs to the field of medicine synthesis, and especially relates to a synthetic method of Pimavanserin. According to the synthetic method, 4-hydroxy benzoic acid is taken as a raw material, esterification reaction, alkylation reaction, hydrolysis, acylation reaction, dehydration reduction, and acylation reaction are carried out to obtain an intermediate (9); fluorobenzylamine and N-methyl-4-piperidone are taken as raw materials for reductive amination to obtain intermediate (10); and at last the intermediate (9) and the intermediate (10) are subjected to aminolysis to obtain finished product Pimavanserin. The initial raw materials are cheap and easily available; reaction conditions are mild; no column chromatography is needed; and the yield is relatively high.

COMPOUNDS, SALTS THEREOF AND METHODS FOR TREATMENT OF DISEASES

The present disclosure relates to compounds according to Formulae disclosed herein, useful for treating diseases.

PROCESSES AND INTERMEDIATES FOR THE PREPARATION OF PIMAVANSERIN

The present disclosure relates to novel, safe and efficient processes for the synthesis of Pimavanserin and salts thereof, as well as novel intermediates that can be used in these processes.

Synthesis method of 4-isobutoxy benzylamine

The invention discloses a synthesis method of 4-isobutoxy benzylamine. 4-hydroxyphenylacetic acid serves as a raw material to generate 4-hydroxyphenylacetic acid methylester through an esterificationreaction; 4-hydroxyphenylacetic acid methylester is subjected to a substitution reaction to generate 4-methyl isobutoxyphenylacetic acid, and 4-isobutoxyphenylacetic acid is obtained after the obtained product is hydrolyzed; 4-isobutoxyphenylacetamide is generated through an acylation reaction; and N-(4-hydroxy benzyl)methyl carbamate is generated through a Hofmann degradation reaction, and a target product is obtained through hydrolysis. The raw materials used in the synthesis method are cheap and easy to get, the reaction condition is mild, post-treatment is simple, column chromatography isnot needed, the product can be obtained easily, and the yield is higher.