Eltoprazine supplier | CasNO.98224-03-4

Name
1-(2,3-DIHYDRO-1,4-BENZODIOXIN-5-YL)-PIPERAZINE HYDROCHLORIDE
EINECS
CAS No. 98224-03-4
Article Data11
CAS DataBase
Density 1.18g/cm³
Solubility
Melting Point
Formula C₁₂H₁₆N₂O₂
Boiling Point 384.3°Cat760mmHg
Molecular Weight 220.271
Flash Point 186.2°C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 1,4-Benzodioxin,piperazine deriv.;1-(2,3-Dihydro-1,4-benzodioxan-5-yl)piperazine;1-(2,3-Dihydro-1,4-benzodioxin-5-yl)piperazine;4-(2,3-Dihydro-1,4-benzodioxin-5-yl)-1-piperazine;4-(2,3-Dihydrobenzo[1,4]dioxin-5-yl)piperazine;N-(2,3-Dihydrobenzo[1,4]dioxin-5-yl)piperazine;Piperazine,1-(2,3-dihydro-1,4-benzodioxin-5-yl)-;
PSA 33.73000
LogP 1.26120

Synthetic route

: 110-85-0
piperazine

5-bromo-2,3-dihydrobenzo[1,4]dioxin: 58328-39-5
5-bromo-2,3-dihydrobenzo[1,4]dioxin

: 98224-03-4
eltoprazine

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 100℃; for 4h; Sealed tube;	59%

: 821-48-7
bis-(2-chloroethyl)amine hydrochloride

: 16081-45-1
1,4-benzodioxan-5-amine

: 98224-03-4
eltoprazine

Conditions

Conditions	Yield
In chlorobenzene Reflux;	51%
With potassium carbonate In chlorobenzene for 24h; Heating;
With sodium hydroxide In chlorobenzene
In sodium hydroxide; chlorobenzene
In sodium hydroxide; chlorobenzene

: 4-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-piperazine-1-carboxylic acid tert-butyl ester

: 98224-03-4
eltoprazine

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane Ambient temperature; Yield given;

: 58328-39-5
5-bromo-2,3-dihydrobenzo[1,4]dioxin

: 98224-03-4
eltoprazine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: tri(o-tolyl)phosphine, bis(dibenzylideneacetone)palladium(O), sodium tert-butoxide / toluene / 100 °C 2: trifluoroacetic acid / CH2Cl2 / Ambient temperature View Scheme

: 4442-53-9
2,3-dihydro-1,4-benzodioxine-5-carboxylic acid

: 98224-03-4
eltoprazine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: triethylamine / water; acetone / 0 °C 2.1: sodium azide / water; acetone 2.2: Heating 3.1: hydrogenchloride / water / Reflux 4.1: chlorobenzene / Reflux View Scheme

: C12H12O6

: 98224-03-4
eltoprazine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium azide / water; acetone 1.2: Heating 2.1: hydrogenchloride / water / Reflux 3.1: chlorobenzene / Reflux View Scheme

: 1155139-88-0
C9H7NO3

: 98224-03-4
eltoprazine

Conditions

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

: 1775-27-5
2-bromoindanone

: 98224-03-4
eltoprazine

: 2-[4-(2,3-dihydrobenzo[1,4]dioxin-5-yl)piperazin-1-yl]-1-indanone

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 48h;	100%

: 3389-21-7
3-(2-bromoethyl)-1H-indole

: 98224-03-4
eltoprazine

: 3-[2-[4-(1,4-Benzodioxan-5-yl)piperazin-1-yl]ethyl]-1H-indole

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; potassium iodide In acetonitrile Heating;	99%

: 50-00-0
formaldehyd

: 98224-03-4
eltoprazine

: 4705-52-6
6,7,8,8a-tetrahydro-5H-imidazo[1,5-a]pyridine-1,3(2H,5H)-dione

: 2-[[4-(2,3-dihydro-1,4-benzodioxan-5-yl)piperazin-1-yl]methyl]-1,3-dioxoperhydroimidazo[1,5-a]pyridine

Conditions

Conditions	Yield
In methanol; water Mannich reaction; Heating;	88%

...Expand

: 98224-03-4
eltoprazine

: 522648-64-2
7-bromo-3-(4-chlorobutyl)-4-fluorobenzo[b]thiophene

: 522649-03-2
1-[4-(7-bromo-4-fluorobenzo[b]thiophen-3-yl)butyl]-4-(2,3-dihydro-benzo[1,4]dioxin-5-yl)piperazine

Conditions

Conditions	Yield
With potassium carbonate; sodium iodide In acetonitrile at 80℃; for 18h;	86%

: 98224-03-4
eltoprazine

: 129722-34-5
7-(4-bromobutoxy)-3,4-dihydro-2(1H)-quinolinone

: 1354030-74-2
7-(4-(4-(2,3-dihydrobenzo[b][1,4]dioxin-5-yl)piperazin-1-yl)butoxy)-3,4-dihydroquinolin-2(1H)-one

Conditions

Conditions	Yield
Stage #1: 7-(4-bromobutoxy)-3,4-dihydro-2(1H)-quinolinone With sodium iodide In acetonitrile for 0.5h; Reflux; Stage #2: eltoprazine With potassium carbonate In acetonitrile for 4h; Reflux;	83%

: 1354030-18-4
4-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-2-yloxy)butyl methanesulfonate

: 98224-03-4
eltoprazine

: 7-(4-(4-(2,3-dihydrobenzo[b][1,4]dioxin-5-yl)piperazin-1-yl)butoxy)-3,4-dihydro-1,8-naphthyridin-2(1H)-one

Conditions

Conditions	Yield
Stage #1: 4-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-2-yloxy)butyl methanesulfonate With sodium iodide In acetonitrile for 0.5h; Reflux; Stage #2: eltoprazine With potassium carbonate In acetonitrile for 4h; Reflux;	83%

: 112-13-0
n-decanoyl chloride

: 98224-03-4
eltoprazine

: 151143-81-6
1-(2,3-dihydro-1,4-benzodioxin-5-yl)-4-(1-oxodecyl)piperazine

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 20℃; for 2h;	80%

: 107-14-2
chloroacetonitrile

: 98224-03-4
eltoprazine

: 161312-72-7
1-(cyanomethyl)-4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazine

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; sodium iodide In N,N-dimethyl-formamide for 2h; Heating;	78%
With triethylamine In 1-methyl-pyrrolidin-2-one

: 98224-03-4
eltoprazine

: 107-07-3
2-chloro-ethanol

: 4-(2,3-dihydro-1,4-benzodioxin-5-yl)-1-piperazineethanol

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; sodium iodide In acetonitrile for 16h; Heating;	78%

: 916263-26-8
tert-butyl (2R)-2-(2-oxoethyl)pyrrolidine-1-carboxylate

: 98224-03-4
eltoprazine

: (R)-tert-butyl 2-{2-[4-(2,3-dihydrobenzo[b][1,4]dioxin-5-yl)piperazin-1-yl]ethyl}pyrrolidine-1-carboxylate

Conditions

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In tetrahydrofuran at 20℃; for 4h;	78%

: 111-64-8
n-octanoic acid chloride

: 98224-03-4
eltoprazine

: 1-(2,3-dihydro-1,4-benzodioxin-5-yl)-4-(1-oxooctyl)piperazine

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 20℃; for 2h;	77%

: 174854-87-6
(S)-4,5-dihydro-5-methyl-3-(2-pyridyl)-3H-[1,2,3]-oxathiazole-2,2-dioxide

: 98224-03-4
eltoprazine

: 187795-96-6
{(R)-2-[4-(2,3-dihydrobenzo[1,4]dioxin-5-yl)piperazin-1-yl]propyl}pyridin-2-ylamine

Conditions

Conditions	Yield
Stage #1: (S)-4,5-dihydro-5-methyl-3-(2-pyridyl)-3H-[1,2,3]-oxathiazole-2,2-dioxide; eltoprazine With potassium carbonate In acetonitrile at 55 - 60℃; for 72h; Stage #2: With hydrogenchloride at 50℃; for 6h;	77%

: 116578-61-1
3-(1H-indol-3-yl)propyl methanesulfonate

: 98224-03-4
eltoprazine

: 3-{3-[4-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-piperazin-1-yl]-propyl}-1H-indole

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; potassium iodide In acetonitrile for 18h; Heating;	77%
With N-ethyl-N,N-diisopropylamine; potassium iodide In acetonitrile for 18h; Heating / reflux;	77%

: 98224-03-4
eltoprazine

: 222991-98-2
2-[4-(2,3-Dihydro[1,4]benzodioxin-5-yl)piperazin-1-yl]-6-methoxy-indan-1-one

Conditions

Conditions	Yield
With potassium carbonate In N-methyl-acetamide; 2-bromo-6-methoxy-2,3-dihydro-1H-inden-1-one; water	74%

: 98224-03-4
eltoprazine

: 219907-04-7
3-chloro-1-(5-nitro-benzo[b]thiophen-3-yl)-propan-1-one

: 433303-53-8
1-(5-nitrobenzo[b]thiophen-3-yl)-3-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]propan-1-one

Conditions

Conditions	Yield
With potassium carbonate In tetrahydrofuran at 20℃; for 72h;	72%

: 98224-03-4
eltoprazine

: 198493-30-0
tert-butyl (2S)-2-(2-oxoethyl)pyrrolidine-1-carboxylate

: (S)-tert-butyl 2-{2-[4-(2,3-dihydrobenzo[b][1,4]dioxin-5-yl)piperazin-1-yl]ethyl}pyrrolidine-1-carboxylate

Conditions

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In tetrahydrofuran at 20℃; for 4h;	72%

: (R)-4,5-dihydro-5-methyl-3-(2-pyridyl)-3H-[1,2,3]-oxathiazole-2,2-dioxide

: 98224-03-4
eltoprazine

: 603992-48-9
{(S)-2-[4-(2,3-dihydrobenzo[1,4]dioxin-5-yl)piperazin-1-yl]propyl}pyridin-2-ylamine

Conditions

Conditions	Yield
Stage #1: (R)-4,5-dihydro-5-methyl-3-(2-pyridyl)-3H-[1,2,3]-oxathiazole-2,2-dioxide; eltoprazine With potassium carbonate In acetonitrile at 55 - 60℃; for 72h; Stage #2: With hydrogenchloride at 50℃; for 6h;	70%

: 98224-03-4
eltoprazine

: 391669-08-2
3-chloro-1-(5-methylbenzo[b]thiophen-3-yl)-1-propanone

: 1-(5-methylbenzo[b]thiophen-3-yl)-3-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]propan-1-one

Conditions

Conditions	Yield
With potassium carbonate In tetrahydrofuran at 20℃; for 72h;	62%

: 5-(4-bromobutoxy)-2-methylbenzo[d]thiazole

: 98224-03-4
eltoprazine

: 5-(4-(4-(2,3-dihydrobenzo[b][1,4]dioxin-5-yl)piperazin-1-yl)-butoxy)-2-methylbenzo[d]thiazole

Conditions

Conditions	Yield
Stage #1: 5-(4-bromobutoxy)-2-methylbenzo[d]thiazole With sodium iodide In acetonitrile for 0.5h; Reflux; Stage #2: eltoprazine In acetonitrile for 6h; Reflux;	61%

: 98-88-4
benzoyl chloride

: 98224-03-4
eltoprazine

: 1-benzoyl-4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazine

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 20℃; for 0.5h;	59%

: 638-29-9
n-valeryl chloride

: 98224-03-4
eltoprazine

: 1-(2,3-dihydro-1,4-benzodioxin-5-yl)-4-(1-oxopentenyl)piperazine

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 20℃; for 2h;	57%

: 2-(chloromethyl)benzimidazole-4-carboxylic acid hydrochloride salt

: 98224-03-4
eltoprazine

: 620950-02-9
2-[[4-(2,3-dihydro-1,4-benzodioxan-5-yl)piperazin-1-yl]methyl]benzimidazole-4-carboxylic acid

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 60℃; for 20h;	57%

: 98224-03-4
eltoprazine

: 2719-27-9
cyclohexanylcarbonyl chloride

: 1-(1-cyclohexylcarbonyl)-4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazine

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 20℃; for 2h;	54%

: 23860-35-7
cyclohexylacetic acid chloride

: 98224-03-4
eltoprazine

: 1-(cyclohexylacetyl)-4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazine

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 20℃; for 2h;	53%

: 98224-03-4
eltoprazine

: 185383-64-6
4-(5-Fluoro-1H-3-indolyl)-cyclohexanone

: 3-{(1,4-cis)-4-[4-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-piperazin-1-yl]-cyclohexyl}-5-fluoro-1H-indole

: 3-{(1,4-trans)-4-[4-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-piperazin-1-yl]-cyclohexyl}-5-fluoro-1H-indole

Conditions

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 20℃; for 12h;	A 53% B 27%
With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane

...Expand

: 282547-09-5
4-(4-fluoro-1H-indol-3-yl)-cyclohexanone

: 98224-03-4
eltoprazine

: 3-{(1,4-cis)-4-[4-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-piperazin-1-yl]-cyclohexyl}-4-fluoro-1H-indole

: 3-{(1,4-trans)-4-[4-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-piperazin-1-yl]-cyclohexyl}-4-fluoro-1H-indole

Conditions

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 20℃; for 12h;	A 53% B 14%

...Expand

: 124369-38-6
1,2-epoxy-6-nitroindane

: 98224-03-4
eltoprazine

: trans-1-[4-(2,3-dihydrobenzo[1,4]dioxin-5-yl)piperid-1-yl] 6-nitroindan-2-ol

Conditions

Conditions	Yield
In acetonitrile for 4h; Heating;	52%

Eltoprazine Chemical Properties

IUPAC Name: 1-(2,3-Dihydro-1,4-benzodioxin-8-yl)piperazine
Synonyms of Eltoprazine (CAS NO.98224-03-4): Eltoprazina ; Eltoprazinum ; 1-(1,4-Benzodioxan-5-yl)piperazine
CAS NO: 98224-03-4
Molecular Formula: C₁₂H₁₆N₂O₂
Molecular Weight: 220.2676
Molecular Structure:
H bond acceptors: 4
H bond donors: 1
Freely Rotating Bonds: 1
Polar Surface Area: 24.94 Å²
Index of Refraction: 1.562
Molar Refractivity: 60.57 cm³
Molar Volume: 186.6 cm³
Surface Tension: 42.5 dyne/cm
Density: 1.18 g/cm³
Flash Point: 186.2 °C
Enthalpy of Vaporization: 63.29 kJ/mol
Boiling Point: 384.3 °C at 760 mmHg
Vapour Pressure: 4.13E-06 mmHg at 25°C
Product Categories of Eltoprazine (CAS NO.98224-03-4): Pyrans, Piperidines &Piperazines;Pyrans, Piperidines & Piperazines
SMILES: O1c2c(OCC1)c(ccc2)N3CCNCC3
InChI: InChI=1/C12H16N2O2/c1-2-10(14-6-4-13-5-7-14)12-11(3-1)15-8-9-16-12/h1-3,13H,4-9H2
InChIKey: WVLHGCRWEHCIOT-UHFFFAOYAT
Std. InChI: InChI=1S/C12H16N2O2/c1-2-10(14-6-4-13-5-7-14)12-11(3-1)15-8-9-16-12/h1-3,13H,4-9H2
Std. InChIKey: WVLHGCRWEHCIOT-UHFFFAOYSA-N

Eltoprazine Uses

Eltoprazine (CAS NO.98224-03-4) is a drug of the phenylpiperazine class which is a serenic or antiaggressive agent. It acts as an agonist at the 5-HT1A and 5-HT1B receptors and as an antagonist at the 5-HT2C receptor.

Product Name

1-(2,3-DIHYDRO-1,4-BENZODIOXIN-5-YL)-PIPERAZINE HYDROCHLORIDE

Synthetic route

Eltoprazine Chemical Properties

Eltoprazine Uses

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