177172-49-5

Basic information

• Product Name: 2-Chloro-N-[(1R)-1-(3-methoxyphenyl)ethyl]-benzenepropanaminehydrochloride
• Synonyms: 2-Chloro-N-[(1R)-1-(3-methoxyphenyl)ethyl]-benzenepropanaminehydrochloride;R 568 hydrochloride;Tecalcet (Hydrochloride);R-568;(R)-3-(2-Chlorophenyl)-N-(1-(3-methoxyphenyl)ethyl)propan-1-amine hydrochloride;3-(2-chlorophenyl)-N-[(1R)-1-(3-methoxyphenyl)ethyl]propan-1-amine, hydrochloride
• CAS NO: 177172-49-5
• Molecular Formula: C18H23Cl2NO
• Molecular Weight: 340.28732
• Mol File: 177172-49-5.mol

Chemical Properties

• Boiling Point: 416.3°C at 760 mmHg
• Flash Point: 205.6°C
• Appearance: /
• Vapor Pressure: 3.86E-07mmHg at 25°C
• Storage Temp.: Desiccate at RT
• CAS DataBase Reference: 2-Chloro-N-[(1R)-1-(3-methoxyphenyl)ethyl]-benzenepropanaminehydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-N-[(1R)-1-(3-methoxyphenyl)ethyl]-benzenepropanaminehydrochloride(177172-49-5)
• EPA Substance Registry System: 2-Chloro-N-[(1R)-1-(3-methoxyphenyl)ethyl]-benzenepropanaminehydrochloride(177172-49-5)

Safety Data

• Hazardous Substances Data: 177172-49-5(Hazardous Substances Data)

Usage

Uses

Used in Treatment of Hyperparathyroidism and Related Disorders:
2-Chloro-N-[(1R)-1-(3-methoxyphenyl)ethyl]-benzenepropanaminehydrochloride is used as a therapeutic agent for the treatment of hyperparathyroidism and related disorders, such as hypercalcemia. Its application is based on its ability to reduce PTH secretion through the modulation of calcium ion receptors on parathyroid cells, thereby helping to restore normal blood calcium concentrations.
Used in Prevention of Vascular Remodeling in Uremia:
In the field of uremic patients, 2-Chloro-N-[(1R)-1-(3-methoxyphenyl)ethyl]-benzenepropanaminehydrochloride is used as a calcimimetic to prevent vascular remodeling. Its application is due to its capacity to positively modulate the human CaSR, which can help in managing the complications associated with uremia.
Used in Research to Explore Novel Actions of CaSR:
2-Chloro-N-[(1R)-1-(3-methoxyphenyl)ethyl]-benzenepropanaminehydrochloride is also utilized in research settings as a tool to investigate the novel actions and potential therapeutic applications of the calcium-sensing receptor (CaSR). This is attributed to its allosteric activation or positive modulation of the human CaSR, which can provide insights into the receptor's role in calcium homeostasis and related physiological processes.
Brand Name:
The brand name for 2-Chloro-N-[(1R)-1-(3-methoxyphenyl)ethyl]-benzenepropanaminehydrochloride is Norcalcin, which is developed by Amgen.

InChI:InChI=1/C18H22ClNO.ClH/c1-14(16-8-5-10-17(13-16)21-2)20-12-6-9-15-7-3-4-11-18(15)19;/h3-5,7-8,10-11,13-14,20H,6,9,12H2,1-2H3;1H/t14-;/m1./s1

Upstream product

• 177172-48-4 (R)-3-(2-chlorophenyl)-N-(1-(3'-methoxyphenyl)ethyl)propanamide 
• 148717-49-1 tecalcet 
• 189289-49-4 [3-(2-Chloro-phenyl)-propyl]-[1-(3-methoxy-phenyl)-eth-(E)-ylidene]-amine 
• 586-37-8 1-(3-Methoxyphenyl)ethanone 
• 18655-48-6 3-(2-chlorophenyl)propan-1-amine 

Relevant articles and documents

Disulfonimide-Catalyzed Asymmetric Reduction of N-Alkyl Imines

A chiral disulfonimide (DSI)-catalyzed asymmetric reduction of N-alkyl imines with Hantzsch esters as a hydrogen source in the presence of Boc2O has been developed. The reaction delivers Boc-protected N-alkyl amines with excellent yields and enantioselectivity. The method tolerates a large variety of alkyl amines, thus illustrating potential for a general reductive cross-coupling of ketones with diverse amines, and it was applied in the synthesis of the pharmaceuticals (S)-Rivastigmine, NPS R-568 Hydrochloride, and (R)-Fendiline. A chiral disulfonimide (DSI)-catalyzed asymmetric reduction of N-alkyl imines with Hantzsch esters as a hydrogen source in the presence of Boc2O was developed. The reaction delivers Boc-protected N-alkyl amines with excellent yields and enantioselectivity. The method was successfully applied to the synthesis of the pharmaceuticals (S)-Rivastigmine, NPS R-568 Hydrochloride, and (R)-Fendiline.

Chemoenzymatic synthesis of the calcimimetics (+)-NPS R-568 via asymmetric reductive acylation of ketoxime intermediate

A practical and efficient procedure for the synthesis of a potent calcimimetic (+)-NPS R-568 was developed. This procedure includes as the key step the asymmetric reductive acylation of a ketoxime intermediate catalyzed by a Pd nanocatalyst and a lipase i

Amine preparation

A method of making (R)-N- 1-(3-methoxyphenyl)ethyl!-3-(2-chlorobenzene)propanamine which involves reducing the appropriate amidyl or iminyl precursor with an appropriate reducing agent. The appropriate amidyl or iminyl precursor is made from a synthesis involving the use of (R)-3-methoxy-α-methylbenzylamine. A method of condensing a nitrile with a primary or secondary amine to form an imine involves the reaction of a nitrile with diisobutylaluminum hydride; and then reacting the resultant compound with a primary or secondary amine to form the imine. The process is especially useful for producing enantiomerically pure chiral imines, and, ultimately, amines. Typical such imines have the formula: STR1 wherein R, R1, R2 and R3 are independently selected from the group consisting of hydrogen, substituted or unsubstituted alkyl, aryl and aralkyl.