89850-72-6

Usage

Uses

Used in Pharmaceutical Synthesis:
4-AMINO-1-PIPERIDINE-ETHANOL is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs. Its unique structure allows for the creation of a variety of medicinal compounds.
Used in Agrochemical Production:
In the agrochemical industry, 4-AMINO-1-PIPERIDINE-ETHANOL is utilized as a building block in the production of various agrochemicals, potentially enhancing crop protection and yield.
Used in Medicinal Chemistry Research:
4-AMINO-1-PIPERIDINE-ETHANOL serves as a valuable compound in medicinal chemistry research, where it is explored for its potential to be incorporated into novel drug candidates, especially for targeting specific biological pathways.
Used in Drug Discovery:
As a component in drug discovery research, 4-AMINO-1-PIPERIDINE-ETHANOL is employed for its potential to be a precursor to new therapeutic agents, contributing to the advancement of medical treatments.

Synthetic route

[1-(2-hydroxyethyl)-piperidin-4-yl]-carbamic acid tert-butyl ester (558443-53-1) → 4-amino-1-(2-hydroxyethyl)piperidine (89850-72-6)

Conditions	Yield
With trifluoroacetic acid at 20℃; for 1h;	95%
With hydrogenchloride In ethanol; water for 2h; Reflux;	95%
With hydrogenchloride In ethanol for 2h; Reflux;	95%
Stage #1: [1-(2-hydroxyethyl)-piperidin-4-yl]-carbamic acid tert-butyl ester With trifluoroacetic acid Stage #2: With hydrogenchloride In methanol at 20℃; for 0.5h; Stage #3: With sodium hydroxide In water at 20℃; for 0.25h; pH=> 10; Cooling with ice;	87%

Br(1-)*C7H11N2O(1+) (51527-83-4) → 4-amino-1-(2-hydroxyethyl)piperidine (89850-72-6)

Conditions	Yield
Stage #1: Br(1-)*C7H11N2O(1+) With hydrogen; sodium; rhodium contaminated with carbon In methanol at 60℃; under 7240.26 Torr; Stage #2: In methanol Reflux;	69%

(piperidin-4-yl)carbamic acid tert-butyl ester (73874-95-0) → 4-amino-1-(2-hydroxyethyl)piperidine (89850-72-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 94 percent / K2CO3 / acetonitrile / 5 h / Heating 2: 95 percent / TFA / 1 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetonitrile / 5 h / Reflux 2.1: trifluoroacetic acid 2.2: 0.5 h / 20 °C 2.3: 0.25 h / 20 °C / pH > 10 / Cooling with ice View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 5 h / Reflux 2: hydrogenchloride / ethanol; water / 2 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 5 h / Reflux 2: hydrogenchloride / ethanol / 2 h / Reflux View Scheme

4-aminopyridine (504-24-5) → 4-amino-1-(2-hydroxyethyl)piperidine (89850-72-6)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: toluene / 3.5 h / Reflux 2.1: hydrogen; sodium / rhodium contaminated with carbon / methanol / 60 °C / 7240.26 Torr 2.2: Amberlyst 15 resin / Reflux View Scheme

2,6-dichloro-N-(2-ethylhexyl)nicotinamide (1421000-02-3) + 4-amino-1-(2-hydroxyethyl)piperidine (89850-72-6) → 6-chloro-N-(2-ethylhexyl)-2-{[1-(2-hydroxyethyl)piperidin-4-yl]amino}nicotinamide (1420999-78-5)

Conditions	Yield
With potassium carbonate In o-xylene for 24h; Reflux;	77.9%
With potassium carbonate In o-xylene for 24h; Reflux;	77.9%

4-iodobenzoic acid (619-58-9) + 4-amino-1-(2-hydroxyethyl)piperidine (89850-72-6) → C14H19IN2O2

Conditions	Yield
With 4-methyl-morpholine; 1-hydroxybenzotriazol-hydrate; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 20h;	50%

4-Bromobenzoic acid (586-76-5) + 4-amino-1-(2-hydroxyethyl)piperidine (89850-72-6) → 4-bromo-N-(1-(2-hydroxyethyl)piperidin-4-yl)benzamide

Conditions	Yield
With 4-methyl-morpholine; 1-hydroxybenzotriazol-hydrate; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 20h;	40%

(R)-1-(3-((3'-(3-bromopropoxy)-2,2'-dimethyl-[1,1'-biphenyl]-3-yl)oxy)propyl)pyrrolidin-3-ol + 4-amino-1-(2-hydroxyethyl)piperidine (89850-72-6) → (R)-1-(3-((3'-(3-((1-(2-hydroxyethyl)piperidin-4-yl)amino)propoxy)-2,2'-dimethyl-[1,1'-biphenyl]-3-yl)oxy)propyl)pyrrolidin-3-ol

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In methanol at 65℃; for 72h; Inert atmosphere;	34%

7-bromo-2-chloroquinoxaline (89891-65-6) + 4-amino-1-(2-hydroxyethyl)piperidine (89850-72-6) → C15H19BrN4O (1345444-82-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 100℃; for 24h;	32%
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 100℃; for 24h;	32%

4-amino-1-(2-hydroxyethyl)piperidine (89850-72-6) + 1H-1,2,3-benzotriazol-1-yl 4-amino-3-methoxybenzoate → 4-amino-N-[1-(2-hydroxy-ethyl)-piperidin-4-yl]-3-methoxy-benzamide (1201694-09-8)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide

7-bromo-2-chloroquinoxaline (89891-65-6) + 4-amino-1-(2-hydroxyethyl)piperidine (89850-72-6) → C30H29F2N7O3 (1345437-78-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 24 h / 100 °C 2: N-ethyl-N,N-diisopropylamine; copper(l) iodide / [Pd0(1,1’-bis(diphenylphosphino)ferrocene)] / dimethyl sulfoxide / 3 h / 90 °C View Scheme
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 24 h / 100 °C 2: N-ethyl-N,N-diisopropylamine / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; copper(l) iodide / dimethyl sulfoxide / 3 h / 90 °C View Scheme

2,6-dichloropyrazine (4774-14-5) + 4-amino-1-(2-hydroxyethyl)piperidine (89850-72-6) → 2-(4-((6-chloropyrazin-2-yl)amino)piperidin-1-yl)ethanol (1401732-37-3)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 100℃; Inert atmosphere;

4-amino-1-(2-hydroxyethyl)piperidine (89850-72-6) → 2-(4-((6-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)pyrazin-2-yl)amino)piperidin-1-yl)ethanol (1401732-38-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 100 °C / Inert atmosphere 2: potassium tert-butylate / 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 12 h / 80 °C / Inert atmosphere View Scheme

4-amino-1-(2-hydroxyethyl)piperidine (89850-72-6) → 2-(4-((6-(3-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)pyrazin-2-yl)amino)piperidin-1-yl)ethanol (1401731-27-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 100 °C / Inert atmosphere 2.1: potassium tert-butylate / 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 12 h / 80 °C / Inert atmosphere 3.1: trifluoroacetic acid / chloroform / 50 °C 3.2: pH 8 View Scheme

3,3-dimethyl-5-oxo-5-(((1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-(2-oxoethyl)-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-yl)oxy)pentanoic acid (1025068-57-8) + 4-amino-1-(2-hydroxyethyl)piperidine (89850-72-6) → 5-(((1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(2-((1-(2-hydroxyethyl)piperidin-4-yl)amino)ethyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-yl)oxy)-3,3-dimethyl-5-oxopentanoic acid

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃;

3,3-dimethyl-5-oxo-5-(((1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-(2-oxoethyl)-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-yl)oxy)pentanoic acid (1025068-57-8) + 4-amino-1-(2-hydroxyethyl)piperidine (89850-72-6) + trifluoroacetic acid (76-05-1) → (3β)-17-[2-[[1-(2-hydroxyethyl)piperidin-4-yl]amino]ethyl]-28-norIup-20(29)-en-3-ol 3-(hydrogen 3,3-dimethyIpentanedioate) bis(trifluoroacetate)

Conditions	Yield
Stage #1: 3,3-dimethyl-5-oxo-5-(((1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-(2-oxoethyl)-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-yl)oxy)pentanoic acid; 4-amino-1-(2-hydroxyethyl)piperidine With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane for 18h; Stage #2: trifluoroacetic acid

phenyl ((1R,4R)-4-((4-((5-cyclopentyl-1H-pyrazol-3-yl)amino)pyrimidin-2-yl)amino)cyclohexyl)carbamate + 4-amino-1-(2-hydroxyethyl)piperidine (89850-72-6) + trifluoroacetic acid (76-05-1) → 1-((1R,4R)-4-((4-((5-cyclopentyl-1H-pyrazol-3-yl)amino)pyrimidin-2-yl)amino)cyclohexyl)-3-(1-(2-hydroxyethyl)piperidin-4-yl)urea 2,2,2-trifluoroacetate

Conditions	Yield
Stage #1: phenyl ((1R,4R)-4-((4-((5-cyclopentyl-1H-pyrazol-3-yl)amino)pyrimidin-2-yl)amino)cyclohexyl)carbamate With triethylamine In N,N-dimethyl-formamide at 85℃; for 1h; Stage #2: 4-amino-1-(2-hydroxyethyl)piperidine In N,N-dimethyl-formamide at 95℃; for 16h; Stage #3: trifluoroacetic acid	25 mg

Upstream product

• 504-24-5 4-aminopyridine 
• 51527-83-4 Br^(1-)*C₇H₁₁N₂O⁽¹⁺⁾ 
• 73874-95-0 (piperidin-4-yl)carbamic acid tert-butyl ester 
• 558443-53-1 [1-(2-hydroxyethyl)-piperidin-4-yl]-carbamic acid tert-butyl ester 

Downstream Products

• 1201694-09-8 4-amino-N-[1-(2-hydroxy-ethyl)-piperidin-4-yl]-3-methoxy-benzamide 
• 1345437-78-6 C₃₀H₂₉F₂N₇O₃ 
• 1401732-38-4 2-(4-((6-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)pyrazin-2-yl)amino)piperidin-1-yl)ethanol 

Relevant academic research and scientific papers

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Disclosed are an anti-angiogenic compound, represented by Chemical Formula I, or a pharmaceutically acceptable salt thereof, a preparation method thereof, and a pharmaceutically acceptable composition including the same. Because the compound of Chemical Formular I potently suppresses the angiogenesis, the compound of Chemical Formula I is applicable to the prevention and treatment of diseases caused by aberrant activity of vascular endothelial growth factor, and available as an anti-angiogenic agent.

Novel Compound Having Angiogenesis Inhibitory Activity, Method for Preparing Same, and Pharmaceutical Composition Comprising Same

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GAS CAPTURE PROCESS

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Synthesis and evaluation of novel radioiodinated benzamides for malignant melanoma

The imaging potential of a series of [123I]benzamides was studied in mice bearing B16F0 melanoma tumors. Compound [123I]25 exhibited tumor uptake >8 %ID/g at 1 h, while that of [123I]14d and [123I]25 reached a maximum of 9-12 %ID/g at 6 h. Standardized uptake values of [123I]14d were higher than 100 between 24 and 72 h after injection. In haloperidol treated animals, the tumor uptake of [ 123I]14d was not significantly different to controls, while significant reduction of [123I]25 uptake was observed, supporting that [123I]14d uptake relates to melanin interaction, whereas part of the mechanism of [123I]25 uptake is related to its σ1-receptor affinity. Benzamides 14d and 25, which display rapid and high tumor uptake, appear to be promising imaging agents for melanoma detection, while 14d, which displays a long lasting and high melanoma/nontarget ratio, is more suitable for evaluation as a potential radiotherapeutic.