179474-79-4

Usage

Uses

Used in Pharmaceutical Industry:
1-(3-Methoxypropyl)-4-piperidinamine is used as a synthetic intermediate for the development of Prucalopride Succinate (P838950), a selective 5-HT4 receptor agonist. 1-(3-Methoxypropyl)-4-piperidinamine is particularly effective in treating chronic constipation and has been approved for use in Europe. Its role in the synthesis of Prucalopride highlights its importance in addressing gastrointestinal disorders and improving patients' quality of life.
While the provided materials do not mention additional applications in different industries, the compound's unique structure suggests that it may have potential uses in other areas, such as chemical research or material science. However, without further information, it is not possible to list specific applications in other industries.

Synthetic route

1-[3-(methyloxy)propyl]-4-piperidinecarboxamide (519147-89-8) → 4-amino-1-(3-methoxypropyl)piperidine (179474-79-4)

Conditions	Yield
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; potassium hydroxide In water; acetonitrile at 5 - 25℃; for 13h;	83%

C22H28N2O → 4-amino-1-(3-methoxypropyl)piperidine (179474-79-4)

Conditions	Yield
With hydrogenchloride In water at 0 - 20℃; pH=1 - 2;	81%

ethyl 1-(3-methoxy-propyl)-piperidin-4-carboxylate (1249604-45-2) → 4-amino-1-(3-methoxypropyl)piperidine (179474-79-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: ammonia / methanol / 60 °C 2: potassium hydroxide; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / water; acetonitrile / 13 h / 5 - 25 °C View Scheme

methyl-1-(3-methoxypropyl)piperidine-4-carboxylate → 4-amino-1-(3-methoxypropyl)piperidine (179474-79-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: ammonium hydroxide / 60 °C 2: potassium hydroxide; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / water; acetonitrile / 13 h / 5 - 25 °C View Scheme

4-aminopiperidine (13035-19-3) → 4-amino-1-(3-methoxypropyl)piperidine (179474-79-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: boron trifluoride diethyl etherate / toluene / Reflux 2.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 2.2: 3 h / 20 °C 3.1: hydrogenchloride / water / 0 - 20 °C / pH 1 - 2 View Scheme

4-amino-1-(3-methoxypropyl)piperidine (179474-79-4) + succinic acid (110-15-6) + 4-amino-5-chloro-2,3-dihydrobenzo[b]furan-7-carboxylic acid (123654-26-2) → prucalopride succinic acid

Conditions	Yield
Stage #1: 4-amino-5-chloro-2,3-dihydrobenzo[b]furan-7-carboxylic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran for 1.5h; Stage #2: 4-amino-1-(3-methoxypropyl)piperidine In tetrahydrofuran at 45℃; for 4h; Stage #3: succinic acid In ethanol at 20℃; for 2h; Solvent; Reagent/catalyst; Temperature;	94%

4-amino-1-(3-methoxypropyl)piperidine (179474-79-4) + 4-amino-5-chloro-2,3-dihydrobenzo[b]furan-7-carboxylic acid (123654-26-2) → prucalopride (179474-81-8)

Conditions	Yield
Stage #1: 4-amino-5-chloro-2,3-dihydrobenzo[b]furan-7-carboxylic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran for 0.416667h; Stage #2: 4-amino-1-(3-methoxypropyl)piperidine In tetrahydrofuran at 45 - 50℃; for 4h;	85%

4-amino-1-(3-methoxypropyl)piperidine (179474-79-4) + 8-chloro-3-methyl-1,7-naphthyridin-2(1H)-one → C18H26N4O2

Conditions	Yield
With Caddick catalyst In 2-methyltetrahydrofuran at 20 - 140℃; for 0.5h; Microwave irradiation;	19%

4-amino-1-(3-methoxypropyl)piperidine (179474-79-4) → 5-AMINO-6-CHLORO-2-METHYL-N-{1-[3-(METHOXY)PROPYL]-4-PIPERIDINYL}IMIDAZO[1,2-a]PYRIDINE-8-CARBOXAMIDE (519147-79-6)

5-amino-6-chloro-2-ethylimidazo[1,2-a]pyridine-8-carboxylic acid (519147-96-7) + 4-amino-1-(3-methoxypropyl)piperidine (179474-79-4) → 5-AMINO-6-CHLORO-2-ETHYL-N-{1-[3-(METHOXY)PROPYL]-4-PIPERIDINYL}IMIDAZO[1,2-a]PYRIDINE-8-CARBOXAMIDE (519148-35-7)

Conditions	Yield
In 5-Amino-N-[(1-butyl-4-piperidinyl)methyl]-6-chloro-2-methylimidazo

4-amino-1-(3-methoxypropyl)piperidine (179474-79-4) + 5-amino-6-chloro-2-propylimidazo[1,2-a]pyridine-8-carboxylic acid (519148-01-7) → 5-amino-6-chloro-2-propyl-N-{1-[3-(methoxy)propyl]-4-piperidinyl}imidazo[1,2-a]pyridine-8-carboxamide (519148-03-9)

Conditions	Yield
In 5-Amino-N-[(1-butyl-4-piperidinyl)methyl]-6-chloro-2-methylimidazo

4-amino-1-(3-methoxypropyl)piperidine (179474-79-4) + 3-(3-t-butyl-5-(3-(naphthalen-1-yl)ureido)-1H-pyrazol-1-yl)benzoic acid (872171-59-0) → C34H42N6O3 (1254308-91-2)

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate

4-amino-1-(3-methoxypropyl)piperidine (179474-79-4) → prucalopride succinic acid

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 0.42 h 1.2: 4 h / 45 - 50 °C 2.1: ethanol / 3 h / 40 °C View Scheme

4-amino-1-(3-methoxypropyl)piperidine (179474-79-4) + 4-amino-5-chloro-7-aldehyde-2,3-dihydrobenzofuran → prucalopride (179474-81-8)

Conditions	Yield
With tert.-butylhydroperoxide; calcium carbonate pentahydrate In acetonitrile at 80℃; for 8h;	36.5 g

4-amino-1-(3-methoxypropyl)piperidine (179474-79-4) + 4-amino-5-chloro-7-hydroxymethyl-2,3-dihydrobenzofuran → prucalopride (179474-81-8)

Conditions	Yield
With tert.-butylhydroperoxide; zinc(II) iodide In acetonitrile at 70℃; for 5h;	33.6 g

4-amino-1-(3-methoxypropyl)piperidine (179474-79-4) + 7-(4-((tert-butoxycarbonyi)(phenethyl)amino)piperidin-1-yl)-2-oxo-2H-chromen-4-yl-trifluoromethanesulfonate → C36H50N4O5

Conditions	Yield
With triethylamine In 1,4-dioxane Reflux;

Upstream product

• 13035-19-3 4-aminopiperidine 
• 519147-89-8 1-[3-(methyloxy)propyl]-4-piperidinecarboxamide 
• 1249604-45-2 ethyl 1-(3-methoxy-propyl)-piperidin-4-carboxylate 

Downstream Products

• 179474-85-2 prucalopride succinate 
• 179474-81-8 prucalopride 

Relevant academic research and scientific papers

A process for preparing 1 - (3 - a oxygen propyl) piperidine - 4 - amine (by machine translation)

The invention discloses a method for preparing 1-(3-methoxypropyl)-4-piperidinamine. The method includes the following steps: the raw material, namely 4-aminopiperdine is adopted, primary amine is selectively protected by benzophenone based on the difference of chemical properties of primary amine and secondary amine, free secondary amine is subjected to proton abstraction, then the free secondary amine subjected to proton abstraction reacts with 3-methoxy-bromopropane, under the acid condition, the protecting group is removed, and finally, the product is obtained. The synthetic process is simple to operate, besides, the removed protecting group subjected to simple treatment can be recycled, and industrial enlarged production is facilitated.

A process for the preparation of intermediate the Pu card must benefit new process (by machine translation)

The invention discloses a compound of formula (I) indicated by the 1 - (3 - a oxygen propyl) - 4 - amino piperdine preparation method, it includes such as the following steps: (1) a compound of formula (II) in the reaction in a solution of ammonia the system results in the type (III) compound; (2) the compound of formula (III) with 1, 3 - dibromo - 5, 5 - dimethyl hydantoin in the reaction under alkaline condition is the system results in the type (I) compound. This preparation method without special reaction equipment requirements, the operation is simple, and is suitable for industrial production; high yield, three wastes, low cost; high purity, heavy metal residue problem. (by machine translation)