221109-26-8

Basic information

• Product Name: 2-PHENYL-3-(4-PIPERIDINYL)-1H-INDOLE
• Synonyms: 2-PHENYL-3-(4-PIPERIDINYL)-1H-INDOLE;2-PHENYL-3-(4-PIPERIDINYL)-2,3-DIHYDRO-1H-INDOLE;2-phenyl-3-(piperidin-4-yl)-1H-indole
• CAS NO: 221109-26-8
• Molecular Formula: C₁₉H₂₀N₂
• Molecular Weight: 276.38
• Product Categories: pharmacetical
• Mol File: 221109-26-8.mol

Chemical Properties

• Boiling Point: 484.065 °C at 760 mmHg
• Flash Point: 246.554 °C
• Appearance: /
• Density: 1.131 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.637
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-PHENYL-3-(4-PIPERIDINYL)-1H-INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PHENYL-3-(4-PIPERIDINYL)-1H-INDOLE(221109-26-8)
• EPA Substance Registry System: 2-PHENYL-3-(4-PIPERIDINYL)-1H-INDOLE(221109-26-8)

Safety Data

• Hazardous Substances Data: 221109-26-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Phenyl-3-(4-piperidinyl)-1H-indole is used as an antipsychotic agent for its potential to treat mental disorders characterized by psychosis, such as schizophrenia. Its ability to modulate the activity of serotonin receptors may contribute to its therapeutic effects in managing psychotic symptoms.
2-Phenyl-3-(4-piperidinyl)-1H-indole is also used as an anti-anxiety agent for its potential to alleviate anxiety disorders by modulating the serotonin system, which plays a crucial role in the regulation of mood and anxiety.
Additionally, 2-Phenyl-3-(4-piperidinyl)-1H-indole is used as a research compound in the field of medicinal chemistry and drug development for its potential as a serotonin receptor agonist. This property allows researchers to study its interactions with the serotonin system and explore its potential therapeutic applications in various psychiatric and neurological disorders.

InChI:InChI=1/C19H20N2/c1-2-6-15(7-3-1)19-18(14-10-12-20-13-11-14)16-8-4-5-9-17(16)21-19/h1-9,14,20-21H,10-13H2

Synthetic route

NH4HCO2 + 2-phenyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole (221109-25-7) → 3-(Piperidin-4-yl)-2-phenyl-1H-indole (221109-26-8)

Conditions	Yield
With sodium hydroxide; palladium In methanol; water	75%

2-phenyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole (221109-25-7) → 3-(Piperidin-4-yl)-2-phenyl-1H-indole (221109-26-8)

Conditions	Yield
With ammonium formate; palladium on activated charcoal In methanol Heating;	75%

piperidin-4-one (41661-47-6) → 3-(Piperidin-4-yl)-2-phenyl-1H-indole (221109-26-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 78 percent / AcOH; H3PO4 / 100 °C 2: 75 percent / ammonium formate / 10 percent Pd/C / methanol / Heating View Scheme

2-phenyl-indole (948-65-2) → 3-(Piperidin-4-yl)-2-phenyl-1H-indole (221109-26-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 78 percent / AcOH; H3PO4 / 100 °C 2: 75 percent / ammonium formate / 10 percent Pd/C / methanol / Heating View Scheme

1-phenyl-2-bromoethane (103-63-9) + 3-(Piperidin-4-yl)-2-phenyl-1H-indole (221109-26-8) → 2-phenyl-3-[1-(2-phenylethyl)piperidin-4-yl]-1H-indole

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide	91%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	90%

benzyl bromide (100-39-0) + 3-(Piperidin-4-yl)-2-phenyl-1H-indole (221109-26-8) → 3-(1-benzylpiperidin-4-yl)-2-phenyl-1H-indole

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	65%
With potassium carbonate In N,N-dimethyl-formamide	65%

3-(Piperidin-4-yl)-2-phenyl-1H-indole (221109-26-8) → 3-(1-methylpiperidin-4-yl)-2-phenyl-1H-indole

Conditions	Yield
With formaldehyd; sodium cyanoborohydride; acetic acid In methanol; water	23%

1-(2-bromo-ethyl)-imidazolidin-2-one + 3-(Piperidin-4-yl)-2-phenyl-1H-indole (221109-26-8) → 1-{2-[4-(2-phenyl-1H-indol-3-yl)-piperidin-1-yl]-ethyl}-imidazolidin-2-one

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	70%

3-(Piperidin-4-yl)-2-phenyl-1H-indole (221109-26-8) + methyl iodide (74-88-4) → 3-(1-methylpiperidin-4-yl)-2-phenyl-1H-indole

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	25%

Upstream product

• 221109-25-7 2-phenyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole 
• 41661-47-6 piperidin-4-one 
• 948-65-2 2-phenyl-indole 

Relevant articles and documents

INDOLE DERIVATIVES USEFUL AS HISTAMINE H3 ANTAGONISTS

Disclosed are novel compounds of the formula I wherein M1 is CH or N and M2 is C(R3) or N; R1 is optionally substituted indolyl or an aza derivative thereof; R2 is optionally substituted aryl or heteroaryl; and the remaining variables are as defined in the specification. Also disclosed are pharmaceutical compositions comprising the compounds of formula I. Also disclosed are methods of treating various diseases or conditions, such as, for example, allergy, allergy-induced airway responses, and congestion (e.g., nasal congestion) using the compounds of Formula I. Also disclosed are methods of treating various diseases or conditions, such as, for example, allergy, allergy-induced airway responses, and congestion (e.g., nasal congestion) using the compounds of formula I in combination with a H1 receptor antagonist.

Phenylindole derivatives as 5-HT2A receptor antagonists

3-(Piperidin-4-yl)-1H-indole derivatives bearing an optionally substituted phenyl moiety at the 2-position of the indole ring system and an alkyl or aryl-alkyl substituent on the nitrogen atom of the piperndine ring are selective antagonists of the human 5-HT2Areceptor. They are therefore useful as pharmaceutical agents, especially in the treatment and/or prevention of adverse conditions of the central nervous system, including psychotic disorders such as schizophrenia.

3-(4-piperidinyl)- and 3-(8-aza-bicyclo[3.2.1]oct-3-yl)-2-phenyl-1H-indoles as bioavailable h5-HT(2A) antagonists

A series of 3-(4-piperidinyl)- and 3-(8-aza-bicyclo[3.2.1]oct-3-yl)-2-phenyl-1H-indoles have been prepared and evaluated as ligands for the h5-HT(2A) receptor. 3-(8-Phenethyl-8-aza-bicyclo[3.2.1]oct-3-yI)-2-phenyl-1H-indole is a high-affinity (1.2nM), selective (>800 fold over h5-HT(2C) and hD2 receptors) antagonist at the h5-HT(2A) receptor with oral bioavailability in rats. (C) 2000 Elsevier Science Ltd.