524-81-2

Basic information

• Product Name: 5-BENZYL-2-METHYL-2,3,4,5-TETRAHYDRO-1H-PYRIDO[4,3-B]INDOLE
• Synonyms: 5-BENZYL-2-METHYL-2,3,4,5-TETRAHYDRO-1H-PYRIDO[4,3-B]INDOLE;MEBHYDROLIN;1H-Pyrido[4,3-b]indole, 2,3,4,5-tetrahydro-2-methyl-5-(phenylmethyl)-;3-Benzyl-6-methyl-1,2,3,4-tetrahydro-gamma-carboline;5-Benzyl-1,3,4,5-tetrahydro-2-methyl-2H-pyrido[4,3-b]indole;Mebhydroline;5-benzyl-1,2,3,4-tetrahydro-2-methylpyrido(4,3-b)indole;2,3,4,5-Tetrahydro-2-methyl-5-(phenylmethyl)-1H-pyrido[4,3-b]indole
• CAS NO: 524-81-2
• Molecular Formula: C₁₉H₂₀N₂
• Molecular Weight: 276.38
• EINECS: 208-364-4
• Product Categories: Intermediates of Sertraline
• Mol File: 524-81-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 95°
• Boiling Point: bp1 207-215°
• Flash Point: 230.4 °C
• Appearance: /
• Density: 1.0246 (rough estimate)
• Vapor Pressure: 3.25E-31mmHg at 25°C
• Refractive Index: 1.5640 (estimate)
• PKA: pKa 2.55 ± 0.18;7.63± 0.04(H2O,t undefined,I=0.30(NaCl)) (Uncertain)
• CAS DataBase Reference: 5-BENZYL-2-METHYL-2,3,4,5-TETRAHYDRO-1H-PYRIDO[4,3-B]INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BENZYL-2-METHYL-2,3,4,5-TETRAHYDRO-1H-PYRIDO[4,3-B]INDOLE(524-81-2)
• EPA Substance Registry System: 5-BENZYL-2-METHYL-2,3,4,5-TETRAHYDRO-1H-PYRIDO[4,3-B]INDOLE(524-81-2)

Safety Data

• Hazardous Substances Data: 524-81-2(Hazardous Substances Data)

Usage

General Description

5-Benzyl-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole is a chemical compound with a complex molecular structure. It is classified as a pyridine and indole derivative, and it is commonly used in organic synthesis and medicinal chemistry. 5-BENZYL-2-METHYL-2,3,4,5-TETRAHYDRO-1H-PYRIDO[4,3-B]INDOLE is of interest due to its potential pharmacological properties, including its potential as an antipsychotic and anxiolytic agent. However, further research is needed to fully understand the biological activities and potential applications of 5-benzyl-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole.

InChI:InChI=1/C19H20N2.C10H8O6S2/c1-20-12-11-19-17(14-20)16-9-5-6-10-18(16)21(19)13-15-7-3-2-4-8-15;11-17(12,13)9-5-1-3-7-8(9)4-2-6-10(7)18(14,15)16/h2-10H,11-14H2,1H3;1-6H,(H,11,12,13)(H,14,15,16)

Synthetic route

mebhydroline 1,5-naphtalenedisulfonate → mebhydrolin (524-81-2)

Conditions	Yield
With sodium hydroxide	97%

3-methyl-9-benzyl-γ-carbolinium chloride → mebhydrolin (524-81-2)

Conditions	Yield
With sodium tetrahydroborate In ethanol at 20℃; for 24h;	73%

1-Methyl-4-piperidone (1445-73-4) + N-benzyl-N-phenylhydrazine (614-31-3) → mebhydrolin (524-81-2)

Conditions	Yield
With hydrogenchloride
With sulfuric acid

benzyl chloride (100-44-7) + sodium-compound of pentadiene-(1.3) → mebhydrolin (524-81-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 88 percent / propan-2-ol / 3.5 h / Heating 2: 73 percent / NaBH4 / aq. ethanol / 24 h / 20 °C View Scheme

2-methyl-2H-pyrido[4,3-b]indole (115191-20-3) → mebhydrolin (524-81-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 88 percent / propan-2-ol / 3.5 h / Heating 2: 73 percent / NaBH4 / aq. ethanol / 24 h / 20 °C View Scheme

1-methyl-4-oxo-piperidine-3-carboxylic acid methyl ester (13221-89-1, 56026-45-0) → mebhydrolin (524-81-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / water / 5.17 h / Reflux 2: 10 h / Reflux View Scheme

1-methylpiperidin-4-one hydrochloride (34737-83-2) + N-benzyl-N-phenylhydrazine (614-31-3) → mebhydrolin (524-81-2)

Conditions	Yield
for 10h; Time; Reflux;

methyl bromide (74-83-9) + mebhydrolin (524-81-2) → 5-Benzyl-2,3,4,5-tetrahydro-2,2-dimethyl-1H-pyrido[4,3-b]indol-2-ium-bromid

Conditions	Yield
In ethanol for 18h; cooling;	94%

mebhydrolin (524-81-2) + chloroacetonitrile (107-14-2) → 5-benzyl-2-cyanomethyl-2-methyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indol-2-ium chloride

Conditions	Yield
In tetrahydrofuran at 20℃;	92%

mebhydrolin (524-81-2) + ethyl bromoacetate (105-36-2) → 5-benzyl-2-(2-ethoxy-2-oxoethyl)-2-methyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indol-2-ium bromide

Conditions	Yield
In tetrahydrofuran at 20℃; for 48h;	91%

mebhydrolin (524-81-2) → 5-Benzyl-2-methyl-1,3,4,5-tetrahydro-pyrido[4,3-b]indole 2-oxide

Conditions	Yield
With dihydrogen peroxide In methanol Heating;	86%

mebhydrolin (524-81-2) + sodium 1,5-naphthalenedisulfonate → bis-(5-benzyl-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole) naphtalene-1,5-disulfonate

Conditions	Yield
In water at 40℃; for 2h;	78%

mebhydrolin (524-81-2) + acetic acid (64-19-7) + 2-acetamido-1-N-(bromoacetyl)-2-deoxy-β-D-glucopyranosylamine (73982-43-1) → 2-acetamido-N-[(9-benzyl-3-methyl-1,2,3,4-tetrahydro-3-carbolinium)acetyl]-2-deoxy-β-D-glucopyranosylamine acetate

Conditions	Yield
Stage #1: mebhydrolin; 2-acetamido-1-N-(bromoacetyl)-2-deoxy-β-D-glucopyranosylamine In methanol at 20℃; for 16h; Stage #2: acetic acid In methanol; water	66%

mebhydrolin (524-81-2) → 1-Benzyl-5-methyl-4,5-dihydro-1H,3H-benzo[b][1,5]diazocine-2,6-dione (210408-31-4) + 5-Benzyl-2-methyl-5H-pyrido[4,3-b]indol-2-ium; perchlorate + 1-Benzyl-1'-methyl-spiro[indolin-2,3'-pyrrolidin]-3-on (210408-29-0) + 5-Benzyl-2-methyl-1,3,4,5-tetrahydro-pyrido[4,3-b]indole 2-oxide + 1-Benzyl-1'-methyl-spiro[indolin-2,3'-pyrrolidin]-3-on-1'-oxid

Conditions	Yield
With sodium periodate In methanol for 24h; Product distribution; Mechanism; Ambient temperature; var. of reagent, temp., ratio, solvent, time;	A 18% B 10% C 12% D 10% E 23%
With sodium periodate In methanol; water for 24h; Product distribution; Mechanism; Ambient temperature; var. of reagent, temp., solvent, ratio, time;	A 18% B 10% C 12% D 10% E 23%

mebhydrolin (524-81-2) → 1-Benzyl-5-methyl-4,5-dihydro-1H,3H-benzo[b][1,5]diazocine-2,6-dione (210408-31-4) + 1-Benzyl-1'-methyl-spiro[indolin-2,3'-pyrrolidin]-3-on (210408-29-0) + 5-Benzyl-2-methyl-1,3,4,5-tetrahydro-pyrido[4,3-b]indole 2-oxide + 1-Benzyl-1'-methyl-spiro[indolin-2,3'-pyrrolidin]-3-on-1'-oxid

Conditions	Yield
With sodium periodate In methanol for 24h; Ambient temperature; Further byproducts given;	A 18% B 12% C 10% D 23%
With sodium periodate In methanol; water for 24h; Ambient temperature; Further byproducts given;	A 18% B 12% C 10% D 23%

mebhydrolin (524-81-2) + benzyl chloride (100-44-7) → 2,5-dibenzyl-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indolium; chloride (119482-83-6)

Conditions	Yield
With acetone

mebhydrolin (524-81-2) + dimethyl sulfate (77-78-1) → 5-benzyl-2,2-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indolium; methyl sulfate (112049-25-9)

Conditions	Yield
With acetone

mebhydrolin (524-81-2) + potassium cyanide (151-50-8) → 5-Benzyl-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-1-carbonitrile (210408-36-9)

Conditions	Yield
With maleic acid; palladium 2) H2O; Yield given. Multistep reaction;
With maleic acid; palladium 1) heating, 2) H2O; Yield given. Multistep reaction;

mebhydrolin (524-81-2) → 5-Benzyl-2-methyl-5H-pyrido[4,3-b]indol-2-ium; perchlorate

Conditions	Yield
With lead(IV) acetate; perchloric acid 1) CHCl3, 1 h; Yield given. Multistep reaction;
With lead(IV) acetate; perchloric acid 1) CHCl3, 1 h, 2) CHCl3; Yield given. Multistep reaction;
Multi-step reaction with 3 steps 1: 1) maleic acid / 1) Pd / 1) heating, 2) H2O 2: 92 percent / HClO4 / ethanol 3: 17 percent / aq. NaOH / 18 h View Scheme
Multi-step reaction with 3 steps 1: 1) maleic acid / 1) Pd / 2) H2O 2: 92 percent / HClO4 / ethanol 3: 17 percent / aq. NaIO4, NaOH / 18 h View Scheme

mebhydrolin (524-81-2) → 5-Benzyl-2-methyl-4,5-dihydro-3H-pyrido[4,3-b]indol-2-ium; perchlorate

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) maleic acid / 1) Pd / 1) heating, 2) H2O 2: 92 percent / HClO4 / ethanol View Scheme
Multi-step reaction with 2 steps 1: 1) maleic acid / 1) Pd / 2) H2O 2: 92 percent / HClO4 / ethanol View Scheme

Upstream product

• 1445-73-4 1-Methyl-4-piperidone 
• 614-31-3 N-benzyl-N-phenylhydrazine 
• 100-44-7 benzyl chloride 
• 34737-83-2 1-methylpiperidin-4-one hydrochloride 
• 13221-89-1 1-methyl-4-oxo-piperidine-3-carboxylic acid methyl ester 
• 115191-20-3 2-methyl-2H-pyrido[4,3-b]indole 

Downstream Products

• 119482-83-6 2,5-dibenzyl-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indolium; chloride 
• 112049-25-9 5-benzyl-2,2-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indolium; methyl sulfate 
• 210408-31-4 1-Benzyl-5-methyl-4,5-dihydro-1H,3H-benzo[b][1,5]diazocine-2,6-dione 
• 210408-29-0 1-Benzyl-1'-methyl-spiro[indolin-2,3'-pyrrolidin]-3-on 
• 210408-36-9 5-Benzyl-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-1-carbonitrile 

Relevant articles and documents

Alternate synthesis for diazoline

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Indole cleavage with mebhydroline by sodium periodate: Part 1: Basic substituted indoles

The reaction behaviour of yohimbine (1), reserpine (5) and mebhydroline (7) as basic substituted indoles against periodate was examined. While 1 and 5 gave only the corresponding amine oxides 2 resp. 6 as definitive products, resulted from 7 beside the N-oxide 8 and stepwise dehydrogenation of the tetrahydro-γ-carboline to 9 and 13 also an attack at the indole system. In this ring contractions led to the spiro compounds 10 and 12 and with ring cleavage and loss of a C-1-unit the dilactam 11 was created.