Iloperidone supplier | CasNO.133454-47-4

Name
Iloperidone
EINECS 603-745-5
CAS No. 133454-47-4
Article Data23
CAS DataBase
Density 1.204 g/cm³
Solubility
Melting Point 118-120°C
Formula C₂₄H₂₇FN₂O₄
Boiling Point 593.7 °C at 760 mmHg
Molecular Weight 426.488
Flash Point 312.8 °C
Transport Information
Appearance
Safety 16-36/37-45
Risk Codes 11-23/24/25-39/23/24/25
Molecular Structure
Hazard Symbols F,T
Synonyms );Iloperidone(Fanapt)
PSA 64.80000
LogP 4.76450

Synthetic route

: 58113-30-7
4-(3-chloropropoxy)-3-methoxyacetophenone

: 84163-13-3
6-fluoro-3-(piperidin-4-yl)benzo[d]isoxazole hydrochloride

: 133454-47-4
iloperidone

Conditions

Conditions	Yield
Stage #1: 6-fluoro-3-(piperidin-4-yl)benzo[d]isoxazole hydrochloride With sodium hydroxide In water at 25 - 30℃; for 0.25h; Industrial scale; Green chemistry; Stage #2: 4-(3-chloropropoxy)-3-methoxyacetophenone In water at 25 - 30℃; for 0.25h; Industrial scale; Green chemistry; Stage #3: With tetrabutylammomium bromide In n-heptane; water at 65 - 70℃; Reagent/catalyst; Solvent; Temperature; Concentration; Time; Industrial scale; Green chemistry;	95%
With sodium hydrogencarbonate In toluene; acetonitrile at 76℃; for 6h; Temperature;	90.5%
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 16h;

: 133454-55-4
4-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-propoxy]-3-methoxy-α-methylbenzenemethanol

: 133454-47-4
iloperidone

Conditions

Conditions	Yield
With oxygen at 120℃; for 10h; Green chemistry;	90%

: 3245-49-6
1-[4-(3-bromopropoxy)-3-methoxyphenyl]ethanone

: 84163-46-2
(2,4-difluorophenyl)(4-piperidinyl)methanone oxime

: 133454-47-4
iloperidone

Conditions

Conditions	Yield
With potassium iodide; lithium hydroxide In ethanol; water at 70℃; for 2h; Temperature; Solvent; Reagent/catalyst;	88.76%

: 917-64-6
methyl magnesium iodide

: 4-[3-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-3-methoxy-benzonitrile

: 133454-47-4
iloperidone

Conditions

Conditions	Yield
Stage #1: methyl magnesium iodide; 4-[3-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-3-methoxy-benzonitrile With copper(l) chloride In diethyl ether; toluene for 2h; Reflux; Stage #2: With sulfuric acid; water In diethyl ether; toluene at 25℃; for 2h; Reflux; Stage #3: With sodium carbonate In diethyl ether; water; toluene	70%

: 329977-73-3
3-(1-(3-chloropropyl)piperidin-4-yl)-6-fluorobenzo[d]isoxazole

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

: 133454-47-4
iloperidone

Conditions

Conditions	Yield
With lithium hydroxide In dichloromethane; water at 180℃; under 33753.4 Torr; Solvent; Flow reactor;	64%
With potassium carbonate In butanone at 78 - 80℃;

: 58113-30-7
4-(3-chloropropoxy)-3-methoxyacetophenone

: 584-08-7
potassium carbonate

: 84163-13-3
6-fluoro-3-(piperidin-4-yl)benzo[d]isoxazole hydrochloride

A: 1400590-28-4
3-(4-acetyl-2-methoxyphenoxy)propyl 4-(6-fluorobenzo[d]isoxazol-3-yl)piperidine-1-carboxylate

B: 133454-47-4
iloperidone

Conditions

Conditions	Yield
In N,N-dimethyl-formamide	A 20% B 58%

...Expand

: 58113-30-7
4-(3-chloropropoxy)-3-methoxyacetophenone

: 584-08-7
potassium carbonate

: 84163-13-3
6-fluoro-3-(piperidin-4-yl)benzo[d]isoxazole hydrochloride

: 133454-47-4
iloperidone

Conditions

Conditions	Yield
In N-methyl-acetamide
In N-methyl-acetamide	5.0 g (58%)
	5.0 g (58%)

...Expand

: 58113-30-7
4-(3-chloropropoxy)-3-methoxyacetophenone

: 133454-47-4
iloperidone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetonitrile / 60 - 85 °C 1.2: 0 - 30 °C 2.1: triethylamine / methanol View Scheme

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

: 133454-47-4
iloperidone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C 2.1: potassium carbonate / acetonitrile / 60 - 85 °C 2.2: 0 - 30 °C 3.1: triethylamine / methanol View Scheme
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 20 h / Reflux 2.1: sodium hydroxide / water / 0.25 h / 25 - 30 °C / Industrial scale; Green chemistry 2.2: 0.25 h / 25 - 30 °C / Industrial scale; Green chemistry 2.3: 65 - 70 °C / Industrial scale; Green chemistry View Scheme
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 25 - 30 °C / Industrial scale; Green chemistry 2.1: sodium hydroxide / water / 0.25 h / 25 - 30 °C / Industrial scale; Green chemistry 2.2: 0.25 h / 25 - 30 °C / Industrial scale; Green chemistry 2.3: 65 - 70 °C / Industrial scale; Green chemistry View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 25 - 30 °C / Industrial scale; Green chemistry 2: N,N-dimethyl-formamide View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 20 h / Reflux 2: N,N-dimethyl-formamide View Scheme

: 84163-13-3
6-fluoro-3-(piperidin-4-yl)benzo[d]isoxazole hydrochloride

: 133454-47-4
iloperidone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetonitrile / 60 - 85 °C 1.2: 0 - 30 °C 2.1: triethylamine / methanol View Scheme

: 1299470-39-5
4'-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidino]propoxy]-3'-methoxyacetophenone hydrochloride

: 133454-47-4
iloperidone

Conditions

Conditions	Yield
With triethylamine In methanol

: 151719-92-5
3-methoxy-4-(3-chloropropoxy) benzaldehyde

: 133454-47-4
iloperidone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: magnesium / diethyl ether / 1 h / Reflux 1.2: 6 h / 0 °C / Reflux 1.3: Cooling with ice 2.1: potassium dichromate; sulfuric acid / diethyl ether; water / 2 h / 10 - 20 °C 3.1: diisopropylamine / methanol / Reflux View Scheme
Multi-step reaction with 3 steps 1.1: hydroxylamine hydrochloride; sodium formate; formic acid / 1 h / Reflux 2.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 9 h / 30 - 90 °C 3.1: copper(l) chloride / toluene; diethyl ether / 2 h / Reflux 3.2: 2 h / 25 °C / Reflux View Scheme

: 121-33-5
vanillin

: 133454-47-4
iloperidone

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: potassium carbonate / acetone / Reflux 2.1: magnesium / diethyl ether / 1 h / Reflux 2.2: 6 h / 0 °C / Reflux 2.3: Cooling with ice 3.1: potassium dichromate; sulfuric acid / diethyl ether; water / 2 h / 10 - 20 °C 4.1: diisopropylamine / methanol / Reflux View Scheme

: 58113-30-7
4-(3-chloropropoxy)-3-methoxyacetophenone

: 84163-77-9
6-fluoro-3-(4-piperidinyl)benzo[d]isoxazole

: 133454-47-4
iloperidone

Conditions

Conditions	Yield
With diisopropylamine In methanol Reflux;
Stage #1: 4-(3-chloropropoxy)-3-methoxyacetophenone; 6-fluoro-3-(4-piperidinyl)benzo[d]isoxazole In water at 30 - 35℃; for 0.5h; Stage #2: With sodium hydroxide In methanol; water at 60℃; for 6.75h; Product distribution / selectivity;

: 58113-30-7
4-(3-chloropropoxy)-3-methoxyacetophenone

: 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole hydrochloride

: 133454-47-4
iloperidone

Conditions

Conditions	Yield
With potassium carbonate; sodium bromide In water; N,N-dimethyl-formamide at 70℃; for 20h;
In N,N-dimethyl-formamide at 90 - 95℃; Concentration;	97 g

: 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole hydrochloride

: 1309041-89-1
4'-(3-p-toluenesulfonylpropoxy)-3'-methoxyacetophenone

: 133454-47-4
iloperidone

Conditions

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 65 - 90℃; for 14h;

: 4421-08-3
3-methoxy-4-hydroxybenzonitrile

: 133454-47-4
iloperidone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetone / 0.08 h / 25 - 30 °C 1.2: 12.5 h / 25 - 30 °C / Reflux 2.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 9 h / 30 - 90 °C 3.1: copper(l) chloride / toluene; diethyl ether / 2 h / Reflux 3.2: 2 h / 25 °C / Reflux View Scheme

: 58113-30-7
4-(3-chloropropoxy)-3-methoxyacetophenone

: 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole hydrochloride

: 584-08-7
potassium carbonate

A: 1400590-28-4
3-(4-acetyl-2-methoxyphenoxy)propyl 4-(6-fluorobenzo[d]isoxazol-3-yl)piperidine-1-carboxylate

B: 133454-47-4
iloperidone

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 90℃; for 16.1667h;

...Expand

: 58113-30-7
4-(3-chloropropoxy)-3-methoxyacetophenone

: 534-17-8
caesium carbonate

: 84163-77-9
6-fluoro-3-(4-piperidinyl)benzo[d]isoxazole

A: 1400590-28-4
3-(4-acetyl-2-methoxyphenoxy)propyl 4-(6-fluorobenzo[d]isoxazol-3-yl)piperidine-1-carboxylate

B: 133454-47-4
iloperidone

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 90℃; for 970h; Product distribution / selectivity;

...Expand

: 84163-13-3
6-fluoro-3-(piperidin-4-yl)benzo[d]isoxazole hydrochloride

: 109-70-6
1,3-chlorobromopropane

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

: 133454-47-4
iloperidone

Conditions

Conditions	Yield
Stage #1: 1.3-chlorobromopropane; 1-(3-methoxy-4-hydroxyphenyl)ethanone With tetrabutylammomium bromide; potassium carbonate In acetonitrile at 80℃; Industry scale; Stage #2: 6-fluoro-3-(piperidin-4-yl)benzo[d]isoxazole hydrochloride With tetrabutylammomium bromide; potassium carbonate In methanol at 60 - 65℃; autoclave;

...Expand

: (Z)-(2,4-difluorophenyl)(piperidin-4-yl)methanone oxime acetate

: 133454-47-4
iloperidone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium hydroxide / water; ethanol / 110 °C / 15001.5 Torr / Flow reactor 2: lithium hydroxide / water; dichloromethane / 125 °C / 15001.5 Torr / Flow reactor 3: lithium hydroxide / water; dichloromethane / 180 °C / 33753.4 Torr / Flow reactor View Scheme

: 84163-77-9
6-fluoro-3-(4-piperidinyl)benzo[d]isoxazole

: 133454-47-4
iloperidone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium hydroxide / water; dichloromethane / 125 °C / 15001.5 Torr / Flow reactor 2: lithium hydroxide / water; dichloromethane / 180 °C / 33753.4 Torr / Flow reactor View Scheme

: 613-70-7
2-methoxyphenyl acetate

: 133454-47-4
iloperidone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: methanesulfonic acid / dichloromethane / 15751.6 Torr / Flow reactor 2: lithium hydroxide / water; dichloromethane / 180 °C / 33753.4 Torr / Flow reactor View Scheme

: 4930-98-7
pyrid-2-ylhydrazine

: 133454-47-4
iloperidone

: (E)-6-fluoro-3-(1-(3-(2-methoxy-4-(1-(2-(pyridin-2-yl)hydrazono)ethyl)phenoxy)propyl)piperidin-4-yl)benzo[d]isoxazole

Conditions

Conditions	Yield
In ethanol at 70℃; for 24h;	90%

: 133454-47-4
iloperidone

: C24H21(2)H6FN2O4

Conditions

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; water-d2; potassium carbonate; silver carbonate In toluene at 90℃; for 12h;	80%

: 133454-47-4
iloperidone

: 133454-55-4
4-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-propoxy]-3-methoxy-α-methylbenzenemethanol

Conditions

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran; methanol for 3h; Ambient temperature;	67%

: 1779-49-3
Methyltriphenylphosphonium bromide

: 133454-47-4
iloperidone

: 6-fluoro-3-[1-[3-[2-methoxy-4-(1-methylethenyl)phenoxy]propyl]-4-piperidinyl]-1,2-benzisoxazole

Conditions

Conditions	Yield
With n-butyllithium 1.) THF, hexane, -65 deg C, 1 h, 2.) THF, hexane, RT, 19 h; Multistep reaction;

: 133454-47-4
iloperidone

: 501373-88-2
(S)-1-(4-{3-[4-(6-fluoro-benzo[d]isoxazol-3-yl)-piperidin-1-yl]-propoxy}-3-methoxyphenyl)-ethanol

Conditions

Conditions	Yield
With borane complex of (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In dichloromethane at 0℃; for 21.5h;
With (3aR,7R)-1-methyl-3,3-diphenyl-tetrahydropyrrolo[1,2-c][1,3,2]oxazaborol In dichloromethane at 0℃; for 20h; Inert atmosphere;

: 133454-47-4
iloperidone

: 1-[4-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-3-methoxyphenyl]ethanone hydrazone

: 133454-47-4
iloperidone

: 1-[4-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-3methoxyphenyl]ethanone oxime

Conditions

Conditions	Yield
With ammonium hydroxide In water

: 1779-49-3
Methyltriphenylphosphonium bromide

: 133454-47-4
iloperidone

A 6-Fluoro]-3-[1-[3-[2-methoxy-4-(1-methylethenyl)phenoxy]propyl]-4-piperidinyl]-1,2-benzisoxazole hydrochloride: 6-Fluoro]-3-[1-[3-[2-methoxy-4-(1-methylethenyl)phenoxy]propyl]-4-piperidinyl]-1,2-benzisoxazole hydrochloride

B: 791-28-6
Triphenylphosphine oxide

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran

...Expand

: 133454-47-4
iloperidone

: 1-[4-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-3-methoxyphenyl]ethanone oxime

Conditions

Conditions	Yield
With ammonium hydroxide In water

: 1779-49-3
Methyltriphenylphosphonium bromide

: 133454-47-4
iloperidone

A: 6-fluoro-3-<1-<3-<2-methoxy-4-(1-methylethenyl)phenoxy>propyl>-4-piperidinyl>-1,2-benzisoxazole hydrochloride

B: 791-28-6
Triphenylphosphine oxide

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran

...Expand

: 133454-47-4
iloperidone

: 1299470-40-8
4'-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidino]propoxy]-3'-methoxyacetophenone phosphate

Conditions

Conditions	Yield
With phosphoric acid In isopropyl alcohol Reflux;

: 133454-47-4
iloperidone

: 1299470-41-9
4'-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidino]propoxy]-3'-methoxyacetophenone bisulphate

Conditions

Conditions	Yield
With sulfuric acid In ethanol Reflux;

: 133454-47-4
iloperidone

: 1299470-39-5
4'-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidino]propoxy]-3'-methoxyacetophenone hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water Reflux;

: 133454-47-4
iloperidone

: 4'-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidino]propoxy]-3'-methoxyacetophenone hydrobromide

Conditions

Conditions	Yield
With hydrogen bromide In ethanol; water Reflux;

: 104-15-4
toluene-4-sulfonic acid

: 133454-47-4
iloperidone

: 1299470-48-6
4'-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidino]propoxy]-3'-methoxyacetophenone p-toluenesulphonate

Conditions

Conditions	Yield
In ethanol Reflux;

: 110-17-8
(2E)-but-2-enedioic acid

: 133454-47-4
iloperidone

: 1299470-45-3
4'-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidino]propoxy]-3'-methoxyacetophenone fumarate

Conditions

Conditions	Yield
In ethanol Reflux;

: 144-62-7
oxalic acid

: 133454-47-4
iloperidone

: 1299470-44-2
4'-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidino]propoxy]-3'-methoxyacetophenone oxalate

Conditions

Conditions	Yield
In ethanol; water Reflux;

: 141-82-2
malonic acid

: 133454-47-4
iloperidone

: 1299470-42-0
4'-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidino]propoxy]-3'-methoxyacetophenone malonate

Conditions

Conditions	Yield
In ethanol Reflux;

: 75-75-2
methanesulfonic acid

: 133454-47-4
iloperidone

: 1299470-47-5
4'-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidino]propoxy]-3'-methoxyacetophenone methanesulphonate

Conditions

Conditions	Yield
In ethanol Reflux;

: 110-15-6
succinic acid

: 133454-47-4
iloperidone

: 1299470-43-1
4'-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidino]propoxy]-3'-methoxyacetophenone succinate

Conditions

Conditions	Yield
In ethanol Reflux;

: 133454-47-4
iloperidone

: 98-11-3
benzenesulfonic acid

: 1299470-46-4
4'-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidino]propoxy]-3'-methoxyacetophenone benzenesulphonate

Conditions

Conditions	Yield
In ethanol Reflux;

Iloperidone Specification

1. Introduction of Iloperidone
Iloperidone is one kind of white to off-white small crystalline powder. The IUPAC Name of this chemical is 1-[4-[3-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl] propoxy]-3-methoxyphenyl]ethanone.
Iloperidone belongs to APIS;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals. Besides, its Classification Code is Antipsychotic.

2. Properties of Iloperidone
Physical properties about Iloperidone are:
(1)Boiling point: 593.7 °C at 760 mmHg; (2)Flash Point: 312.8 °C; (3)Density: 1.204 g/cm³; (4)Surface Tension: 45.2 dyne/cm; (5)Enthalpy of Vaporization: 88.5 kJ/mol; (6)Vapour Pressure: 4.6E-14 mmHg at 25°C; (7)XLogP3-AA: 4.1; (8)H-Bond Donor: 0; (9)H-Bond Acceptor: 7; (10)XLogP3-AA: 4.1; (11)H-Bond Donor: 0; (12)H-Bond Acceptor: 7; (13)Rotatable Bond Count: 8; (14)Tautomer Count: 2; (15)Exact Mass: 426.195486; (16)MonoIsotopic Mass: 426.195486; (17)Topological Polar Surface Area: 64.8; (18)Heavy Atom Count: 31; (19)Formal Charge: 0; (20)Complexity: 586; (21)Isotope Atom Count: 0; (22)Defined Atom Stereocenter Count: 0; (23)Undefined Atom Stereocenter Count: 0; (24)Defined Bond Stereocenter Count: 0; (25)Undefined Bond Stereocenter Count: 0; (26)Covalently-Bonded Unit Count: 1; (27)Feature 3D Acceptor Count: 4; (28)Feature 3D Cation Count: 1; (29)Feature 3D Ring Count: 4; (30)Effective Rotor Count: 9.2; (31)Conformer Sampling RMSD: 1; (32)CID Conformer Count: 428.

3. Structure Descriptors of Iloperidone
(1)Canonical SMILES: CC(=O)C1=CC(=C(C=C1)OCCCN2CCC(CC2)C3=NOC4=C3C=CC(=C4)F)OC
(2)InChI: InChI=1S/C24H27FN2O4/c1-16(28)18-4-7-21(23(14-18)29-2)30-13-3-10-27-11-8-17(9-12-27)24-20-6-5-19(25)15-22(20)31-26-24/h4-7,14-15,17H,3,8-13H2,1-2H3
(3)InChIKey: XMXHEBAFVSFQEX-UHFFFAOYSA-N

4. Uses of Iloperidone
Iloperidone is an antipsychotic. Iloperidone is Combined dopamine (D2) and serotonin (5HT2) receptor antagonist. In addition, it is also an atypical, negative symptom antipsychotic agent. Iloperidone is an atypical antipsychotic for the treatment of schizophrenia. It was approved by the U.S. Food and Drug Administration (FDA) for use in the United States on May 6, 2009.R46:May cause heritable genetic damage.

Product Name

Iloperidone

Synthetic route

Iloperidone Specification

Related Products

Hot Products