98092-92-3

Basic information

• Product Name: 2-[3-(4-propylheptyl)morpholin-4-yl]ethanol
• Synonyms: 2-[3-(4-propylheptyl)morpholin-4-yl]ethanol
• CAS NO: 98092-92-3
• Molecular Formula: C₁₆H₃₃NO₂*ClH
• Molecular Weight: 307.9
• Mol File: 98092-92-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 70-72°
• Boiling Point: 374.6°Cat760mmHg
• Flash Point: 180.3°C
• Appearance: /
• Density: 0.924g/cm³
• Vapor Pressure: 0.003Pa at 25℃
• PKA: 7.1(at 25℃)
• CAS DataBase Reference: 2-[3-(4-propylheptyl)morpholin-4-yl]ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[3-(4-propylheptyl)morpholin-4-yl]ethanol(98092-92-3)
• EPA Substance Registry System: 2-[3-(4-propylheptyl)morpholin-4-yl]ethanol(98092-92-3)

Safety Data

• Hazardous Substances Data: 98092-92-3(Hazardous Substances Data)

Usage

General Description

2-[3-(4-propylheptyl)morpholin-4-yl]ethanol is a chemical compound that belongs to the class of morpholine derivatives. It contains a morpholine ring with a propylheptyl group attached to it. The compound also has an ethanol group attached to the morpholine ring. This chemical is used in the synthesis of pharmaceuticals and may have potential therapeutic applications due to its structural similarity to other biologically active compounds. It is important to handle this compound with caution as its properties and potential toxicity have not been fully studied.

Synthetic route

3-(4-propyl-heptyl)-4-(2-hydroxyethyl)-morpholine (79874-76-3) → rac-4-(2-hydroxyethyl)-3-(4-propylheptyl) morpholine hydrochloride (98092-92-3)

Conditions	Yield
With hydrogenchloride In dibutyl ether; water; ethyl acetate at 0 - 60℃; for 3h; Product distribution / selectivity;	67%
With hydrogenchloride In water at 0 - 60℃; for 4h; Product distribution / selectivity;	50%
With hydrogenchloride In water; 4-methyl-2-pentanone at 0 - 60℃; for 2h;
With hydrogenchloride In Isopropyl acetate at 0℃;	93.5 g

4-(2-hydroxyethyl)morpholin-3-one (41036-01-5) → rac-4-(2-hydroxyethyl)-3-(4-propylheptyl) morpholine hydrochloride (98092-92-3)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: lithium hydride / tetrahydrofuran / 20 °C / Reflux 1.2: 20 °C / Reflux 2.1: hydrogen; 5%-palladium/activated carbon / methanol / 30 °C / 2250.23 Torr 3.1: hydrogenchloride / Isopropyl acetate / 0 °C View Scheme

8a-(4-propylhept-3-en-1-yl)hexahydrooxazolo[2,3-c][1,4]oxazine → rac-4-(2-hydroxyethyl)-3-(4-propylheptyl) morpholine hydrochloride (98092-92-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen; 5%-palladium/activated carbon / methanol / 30 °C / 2250.23 Torr 2: hydrogenchloride / Isopropyl acetate / 0 °C View Scheme

4-cyclopropylheptan-4-ol (57583-50-3) → rac-4-(2-hydroxyethyl)-3-(4-propylheptyl) morpholine hydrochloride (98092-92-3)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: hydrogenchloride / water / 10 h / 20 - 40 °C / Large scale 2.1: lithium hydride / tetrahydrofuran / 20 °C / Reflux 2.2: 20 °C / Reflux 3.1: hydrogen; 5%-palladium/activated carbon / methanol / 30 °C / 2250.23 Torr 4.1: hydrogenchloride / Isopropyl acetate / 0 °C View Scheme

1-chloro-4-propylhept-3-ene → rac-4-(2-hydroxyethyl)-3-(4-propylheptyl) morpholine hydrochloride (98092-92-3)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: lithium hydride / tetrahydrofuran / 20 °C / Reflux 1.2: 20 °C / Reflux 2.1: hydrogen; 5%-palladium/activated carbon / methanol / 30 °C / 2250.23 Torr 3.1: hydrogenchloride / Isopropyl acetate / 0 °C View Scheme

Upstream product

• 79874-76-3 3-(4-propyl-heptyl)-4-(2-hydroxyethyl)-morpholine 
• 57583-50-3 4-cyclopropylheptan-4-ol 
• 41036-01-5 4-(2-hydroxyethyl)morpholin-3-one 

Relevant articles and documents

METHOD FOR THE MANUFACTURING OF 2-(3-(ALKYL AND ALKENYL)MORPHOLINO)-ETHAN-1-OLS

The present invention relates to a method for the manufacture of 2-(3-(alkyl or alkenyl)morpholino)-ethan-1-ols by reduction of 8a-(alkyl and alkenyl)hexahydrooxazolo[2,3-c][1,4]oxazines encompassing a process for producing 2-(3-(4-propylheptyl)morpholino)ethan-1-ol with the INN name delmopinol. The invention also relates to 1-chloro-4-propylhept-3-ene, 1-iodo-4-propylhept-3-ene, 8a-(4-5 propylheptyl)hexahydrooxazolo[2,3-c][1,4]oxazine, 8a-(4-propylhept-3-en-1-yl)hexahydrooxazolo[2,3-c][1,4]oxazine and 2-(3-(4-propylhept-3-en-1-yl)morpholino)ethan-1-ol which are intermediates in the delmopinol process.

PROCESS FOR THE PREPARATION OF DELMOPINOL AND DERIVATIVES THEREOF

A process for the preparation of delmopinol (3-(4-propylheptyl)-4-morpholinethanol) or a derivative or a pharmaceutically acceptable salt, or a solvate thereof, including an hydrate, comprises reacting oxazolidin [2, 3-c] morpholine and a grignard reagent, and optionally converting the delmopinol (or derivative) free base into a pharmaceutically acceptable salt. The oxazolidin [2, 3-c] morpholine and the grignard reagent are useful as intermediates in the production process.