98092-92-3

Usage

Uses

Used in Pharmaceutical Synthesis:
2-[3-(4-propylheptyl)morpholin-4-yl]ethanol is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs with potential therapeutic benefits.
Used in Drug Discovery:
In the field of drug discovery, 2-[3-(4-propylheptyl)morpholin-4-yl]ethanol is utilized as a structural template for designing and developing novel compounds with potential medicinal properties, leveraging its morpholine and propylheptyl groups for enhanced bioactivity.
Used in Chemical Research:
2-[3-(4-propylheptyl)morpholin-4-yl]ethanol serves as a subject of chemical research to explore its properties, reactivity, and potential applications in various chemical processes, including the development of new synthetic pathways and methodologies.

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

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

Relevant academic research and scientific papers

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.

PREPARATION OF DELMOPINOL

It comprises a process for the production of delmopinol or a pharmaceutically acceptable salt and/or a solvate thereof, by subjecting the compound of formula (II) where R1 and R2 are the same or different, independently selected from the group consisting of H, (C1-C6) alkyl or, alternatively, R1 and R2 form, together with the carbon atom to which they are attached, a (C5-C6) cycloalkyl radical; and R3 is a radical selected from the group consisting of CF3, (C1-C4) alkyl, phenyl, and phenyl mono- ordisubstituted by a radical selected from the group consisting of (C1-C4)-alkyl, halogen and nitro to a deprotection and cyclisation reaction. The process is useful to prepare delmopinol or its salts on an industrial scale. The compound of formula (II) is new and also forms part of the present invention, as well as its preparation process and other new intermediates of said preparation 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.