Product Name

  • Name

    5-BENZYL-2-METHYL-2,3,4,5-TETRAHYDRO-1H-PYRIDO[4,3-B]INDOLE

  • EINECS 208-364-4
  • CAS No. 524-81-2
  • Article Data6
  • CAS DataBase
  • Density 1.12 g/cm3
  • Solubility
  • Melting Point 95°
  • Formula C19H20N2
  • Boiling Point 457.3 °C at 760 mmHg
  • Molecular Weight 276.381
  • Flash Point 230.4 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 524-81-2 (5-BENZYL-2-METHYL-2,3,4,5-TETRAHYDRO-1H-PYRIDO[4,3-B]INDOLE)
  • Hazard Symbols
  • Synonyms 1H-Pyrido[4,3-b]indole,5-benzyl-2,3,4,5-tetrahydro-2-methyl- (7CI);2H-Pyrido[4,3-b]indole,5-benzyl-1,3,4,5-tetrahydro-2-methyl- (6CI);3-Methyl-9-benzyl-1,2,3,4-tetrahydro-g-carboline;5-Benzyl-1,2,3,4-tetrahydro-2-methyl-g-carboline;5-Benzyl-1,3,4,5-tetrahydro-2-methyl-2H-pyrido[4,3-b]indole;Mebhydrolin;N-Methyl-9-benzyltetrahydro-g-carboline;
  • PSA 8.17000
  • LogP 3.61540

Synthetic route

mebhydroline 1,5-naphtalenedisulfonate

mebhydroline 1,5-naphtalenedisulfonate

mebhydrolin
524-81-2

mebhydrolin

Conditions
ConditionsYield
With sodium hydroxide97%
3-methyl-9-benzyl-γ-carbolinium chloride

3-methyl-9-benzyl-γ-carbolinium chloride

mebhydrolin
524-81-2

mebhydrolin

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol at 20℃; for 24h;73%
1-Methyl-4-piperidone
1445-73-4

1-Methyl-4-piperidone

N-benzyl-N-phenylhydrazine
614-31-3

N-benzyl-N-phenylhydrazine

mebhydrolin
524-81-2

mebhydrolin

Conditions
ConditionsYield
With hydrogenchloride
With sulfuric acid
benzyl chloride
100-44-7

benzyl chloride

sodium-compound of pentadiene-(1.3)

sodium-compound of pentadiene-(1.3)

mebhydrolin
524-81-2

mebhydrolin

Conditions
ConditionsYield
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

2-methyl-2H-pyrido[4,3-b]indole

mebhydrolin
524-81-2

mebhydrolin

Conditions
ConditionsYield
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

1-methyl-4-oxo-piperidine-3-carboxylic acid methyl ester

mebhydrolin
524-81-2

mebhydrolin

Conditions
ConditionsYield
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

1-methylpiperidin-4-one hydrochloride

N-benzyl-N-phenylhydrazine
614-31-3

N-benzyl-N-phenylhydrazine

mebhydrolin
524-81-2

mebhydrolin

Conditions
ConditionsYield
for 10h; Time; Reflux;
methyl bromide
74-83-9

methyl bromide

mebhydrolin
524-81-2

mebhydrolin

5-Benzyl-2,3,4,5-tetrahydro-2,2-dimethyl-1H-pyrido[4,3-b]indol-2-ium-bromid

5-Benzyl-2,3,4,5-tetrahydro-2,2-dimethyl-1H-pyrido[4,3-b]indol-2-ium-bromid

Conditions
ConditionsYield
In ethanol for 18h; cooling;94%
mebhydrolin
524-81-2

mebhydrolin

chloroacetonitrile
107-14-2

chloroacetonitrile

5-benzyl-2-cyanomethyl-2-methyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indol-2-ium chloride

5-benzyl-2-cyanomethyl-2-methyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indol-2-ium chloride

Conditions
ConditionsYield
In tetrahydrofuran at 20℃;92%
mebhydrolin
524-81-2

mebhydrolin

ethyl bromoacetate
105-36-2

ethyl bromoacetate

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

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
ConditionsYield
In tetrahydrofuran at 20℃; for 48h;91%
mebhydrolin
524-81-2

mebhydrolin

5-Benzyl-2-methyl-1,3,4,5-tetrahydro-pyrido[4,3-b]indole 2-oxide

5-Benzyl-2-methyl-1,3,4,5-tetrahydro-pyrido[4,3-b]indole 2-oxide

Conditions
ConditionsYield
With dihydrogen peroxide In methanol Heating;86%
mebhydrolin
524-81-2

mebhydrolin

sodium 1,5-naphthalenedisulfonate

sodium 1,5-naphthalenedisulfonate

bis-(5-benzyl-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole) naphtalene-1,5-disulfonate

bis-(5-benzyl-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole) naphtalene-1,5-disulfonate

Conditions
ConditionsYield
In water at 40℃; for 2h;78%
mebhydrolin
524-81-2

mebhydrolin

acetic acid
64-19-7

acetic acid

2-acetamido-1-N-(bromoacetyl)-2-deoxy-β-D-glucopyranosylamine
73982-43-1

2-acetamido-1-N-(bromoacetyl)-2-deoxy-β-D-glucopyranosylamine

2-acetamido-N-[(9-benzyl-3-methyl-1,2,3,4-tetrahydro-3-carbolinium)acetyl]-2-deoxy-β-D-glucopyranosylamine acetate

2-acetamido-N-[(9-benzyl-3-methyl-1,2,3,4-tetrahydro-3-carbolinium)acetyl]-2-deoxy-β-D-glucopyranosylamine acetate

Conditions
ConditionsYield
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%
...Expand
mebhydrolin
524-81-2

mebhydrolin

A

1-Benzyl-5-methyl-4,5-dihydro-1H,3H-benzo[b][1,5]diazocine-2,6-dione
210408-31-4

1-Benzyl-5-methyl-4,5-dihydro-1H,3H-benzo[b][1,5]diazocine-2,6-dione

B

5-Benzyl-2-methyl-5H-pyrido[4,3-b]indol-2-ium; perchlorate

5-Benzyl-2-methyl-5H-pyrido[4,3-b]indol-2-ium; perchlorate

C

1-Benzyl-1'-methyl-spiro[indolin-2,3'-pyrrolidin]-3-on
210408-29-0

1-Benzyl-1'-methyl-spiro[indolin-2,3'-pyrrolidin]-3-on

D

5-Benzyl-2-methyl-1,3,4,5-tetrahydro-pyrido[4,3-b]indole 2-oxide

5-Benzyl-2-methyl-1,3,4,5-tetrahydro-pyrido[4,3-b]indole 2-oxide

E

1-Benzyl-1'-methyl-spiro[indolin-2,3'-pyrrolidin]-3-on-1'-oxid

1-Benzyl-1'-methyl-spiro[indolin-2,3'-pyrrolidin]-3-on-1'-oxid

Conditions
ConditionsYield
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%
...Expand
mebhydrolin
524-81-2

mebhydrolin

A

1-Benzyl-5-methyl-4,5-dihydro-1H,3H-benzo[b][1,5]diazocine-2,6-dione
210408-31-4

1-Benzyl-5-methyl-4,5-dihydro-1H,3H-benzo[b][1,5]diazocine-2,6-dione

B

1-Benzyl-1'-methyl-spiro[indolin-2,3'-pyrrolidin]-3-on
210408-29-0

1-Benzyl-1'-methyl-spiro[indolin-2,3'-pyrrolidin]-3-on

C

5-Benzyl-2-methyl-1,3,4,5-tetrahydro-pyrido[4,3-b]indole 2-oxide

5-Benzyl-2-methyl-1,3,4,5-tetrahydro-pyrido[4,3-b]indole 2-oxide

D

1-Benzyl-1'-methyl-spiro[indolin-2,3'-pyrrolidin]-3-on-1'-oxid

1-Benzyl-1'-methyl-spiro[indolin-2,3'-pyrrolidin]-3-on-1'-oxid

Conditions
ConditionsYield
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%
...Expand
mebhydrolin
524-81-2

mebhydrolin

benzyl chloride
100-44-7

benzyl chloride

2,5-dibenzyl-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indolium; chloride
119482-83-6

2,5-dibenzyl-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indolium; chloride

Conditions
ConditionsYield
With acetone
mebhydrolin
524-81-2

mebhydrolin

dimethyl sulfate
77-78-1

dimethyl sulfate

5-benzyl-2,2-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indolium; methyl sulfate
112049-25-9

5-benzyl-2,2-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indolium; methyl sulfate

Conditions
ConditionsYield
With acetone
mebhydrolin
524-81-2

mebhydrolin

potassium cyanide
151-50-8

potassium cyanide

5-Benzyl-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-1-carbonitrile
210408-36-9

5-Benzyl-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-1-carbonitrile

Conditions
ConditionsYield
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

mebhydrolin

5-Benzyl-2-methyl-5H-pyrido[4,3-b]indol-2-ium; perchlorate

5-Benzyl-2-methyl-5H-pyrido[4,3-b]indol-2-ium; perchlorate

Conditions
ConditionsYield
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

mebhydrolin

5-Benzyl-2-methyl-4,5-dihydro-3H-pyrido[4,3-b]indol-2-ium; perchlorate

5-Benzyl-2-methyl-4,5-dihydro-3H-pyrido[4,3-b]indol-2-ium; perchlorate

Conditions
ConditionsYield
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

1H-Pyrido[4,3-b]indole,2,3,4,5-tetrahydro-2-methyl-5-(phenylmethyl)- Specification

The 1H-Pyrido[4,3-b]indole,2,3,4,5-tetrahydro-2-methyl-5-(phenylmethyl)-, with CAS registry number 524-81-2, belongs to the following product category: Intermediates of Sertraline. It has the systematic name of 5-benzyl-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole. And the chemical formula of this chemical is C19H20N2.

Physical properties of 1H-Pyrido[4,3-b]indole,2,3,4,5-tetrahydro-2-methyl-5-(phenylmethyl)-: (1)ACD/LogP: 4.10; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.11; (4)ACD/LogD (pH 7.4): 2.39; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 15.04; (7)ACD/KOC (pH 5.5): 4.18; (8)ACD/KOC (pH 7.4): 79.24; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 8.17 Å2; (13)Index of Refraction: 1.633; (14)Molar Refractivity: 87.64 cm3; (15)Molar Volume: 245.1 cm3; (16)Polarizability: 34.74×10-24cm3; (17)Surface Tension: 43.4 dyne/cm; (18)Density: 1.12 g/cm3; (19)Flash Point: 230.4 °C; (20)Enthalpy of Vaporization: 71.74 kJ/mol; (21)Boiling Point: 457.3 °C at 760 mmHg; (22)Vapour Pressure: 1.51E-08 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: c12c4c(n(c1CCN(C2)C)Cc3ccccc3)cccc4
(2)InChI: InChI=1/C19H20N2/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/h2-10H,11-14H2,1H3
(3)InChIKey: FQQIIPAOSKSOJM-UHFFFAOYAM
(4)Std. InChI: InChI=1S/C19H20N2/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/h2-10H,11-14H2,1H3
(5)Std. InChIKey: FQQIIPAOSKSOJM-UHFFFAOYSA-N

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