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303-26-4

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303-26-4 Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 303-26-4 differently. You can refer to the following data:
1. A metabolite of Cetirizine (C281100) and Hydroxyzine. Citirizine impurity A.
2. Cetrizine Dihydrochloride intermediate

Preparation

Preparation of 1-[(4-chlorophenyl)phenylmethyl]piperazine. (CPMP)About 0.5 mL of DMF, 0.1 g of KI and 10 g (0.12 mol) of piperazine were mixed with 15 mL of toluene and heated to 80oC for 0.5 h. This mixture at 80oC was mixed with 4-CBC in toluene and the temperature was maintained at 80oC for a period of 2 h followed by refluxing at the same temperature for 12h. The reaction mixture was then cooled to 20oC. The toluene layer was washed twice with 20 mL of water and treated with HCl (15 mL conc. HCl in 5mL of water) at 5-10oC. The reaction mixture was filtered and the aqueous layer was separated from the filtrate. About 10 mL of toluene and 10 mL of methylene dichloride (MDC) washes were given to the aqueous layer and neutralized with 22 mL of 30 % NaOH solution at 10oC and maintained at 20oC for 2h. The solid compound formed was filtered, sucked and dried at 50oC for 3 h.Yield: 92 %; m.p: 63-65oC.

Flammability and Explosibility

Notclassified

Safety Profile

An experimental teratogen.Experimental reproductive effects. When heated todecomposition it emits very toxic fumes of NOx and Clí.

Check Digit Verification of cas no

The CAS Registry Mumber 303-26-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,0 and 3 respectively; the second part has 2 digits, 2 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 303-26:
(5*3)+(4*0)+(3*3)+(2*2)+(1*6)=34
34 % 10 = 4
So 303-26-4 is a valid CAS Registry Number.
InChI:InChI=1/C17H19ClN2/c18-16-8-6-15(7-9-16)17(14-4-2-1-3-5-14)20-12-10-19-11-13-20/h1-9,17,19H,10-13H2/p+2/t17-/m0/s1

303-26-4 Well-known Company Product Price

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  • Detail
  • Alfa Aesar

  • (H55970)  1-(4-Chlorobenzhydryl)piperazine, tech. 90%   

  • 303-26-4

  • 250mg

  • 112.0CNY

  • Detail
  • Alfa Aesar

  • (H55970)  1-(4-Chlorobenzhydryl)piperazine, tech. 90%   

  • 303-26-4

  • 1g

  • 314.0CNY

  • Detail
  • Alfa Aesar

  • (H55970)  1-(4-Chlorobenzhydryl)piperazine, tech. 90%   

  • 303-26-4

  • 5g

  • 1062.0CNY

  • Detail
  • Sigma-Aldrich

  • (C0980651)  CetirizineimpurityA  European Pharmacopoeia (EP) Reference Standard

  • 303-26-4

  • C0980651

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (Y0001311)  MeclozineimpurityH  European Pharmacopoeia (EP) Reference Standard

  • 303-26-4

  • Y0001311

  • 1,880.19CNY

  • Detail
  • USP

  • (1333058)  HydroxyzineRelatedCompoundA  United States Pharmacopeia (USP) Reference Standard

  • 303-26-4

  • 1333058-25MG

  • 14,578.20CNY

  • Detail
  • Aldrich

  • (C24507)  1-(4-Chlorobenzhydryl)piperazine  technical grade, 90%

  • 303-26-4

  • C24507-1G

  • 530.01CNY

  • Detail

303-26-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-(4-Chlorobenzhydryl)piperazine

1.2 Other means of identification

Product number -
Other names N-[1-(4-chlorophenyl)-1-(phenyl)methyl]piperazine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:303-26-4 SDS

303-26-4Synthetic route

1-[(4-chlorophenyl)phenylmethyl]-4-[(4-methylphenyl)sulfonyl]piperazine

1-[(4-chlorophenyl)phenylmethyl]-4-[(4-methylphenyl)sulfonyl]piperazine

4-hydroxy-benzoic acid
99-96-7

4-hydroxy-benzoic acid

N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

Conditions
ConditionsYield
With sodium hydroxide; sodium chloride; hydrogen bromide In hexane; water; acetic acid; toluene84.8%
piperazine
110-85-0

piperazine

1-chloro-4-(chloro(phenyl)methyl)benzene
134-83-8

1-chloro-4-(chloro(phenyl)methyl)benzene

N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

Conditions
ConditionsYield
With K2CO3; Ki In dichloromethane; butanone57%
With Ki; potassium carbonate In dichloromethane; butanone57%
With Ki; potassium carbonate In dichloromethane; butanone57%
piperazine-1-carbaldehyde
7755-92-2

piperazine-1-carbaldehyde

1-chloro-4-(chloro(phenyl)methyl)benzene
134-83-8

1-chloro-4-(chloro(phenyl)methyl)benzene

N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

Conditions
ConditionsYield
With hydrogenchloride
With sodium hydroxide
(+-)-1-benzyl-4-<4-chloro-benzhydryl>-piperazine

(+-)-1-benzyl-4-<4-chloro-benzhydryl>-piperazine

N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

Conditions
ConditionsYield
With ethanol; nickel at 150℃; under 73550.8 Torr; Hydrogenation;
(+-)-4-<4-chloro-benzhydryl>-piperazine-1-carboxylic acid ethyl ester

(+-)-4-<4-chloro-benzhydryl>-piperazine-1-carboxylic acid ethyl ester

N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

Conditions
ConditionsYield
With potassium hydroxide
With hydrogenchloride
(R)-(+)-4-(4-chlorophenyl)-phenylmethyl-piperazine-1-carboxylic acid-2,2,2-trichloroethylester hydrochloride
941576-98-3

(R)-(+)-4-(4-chlorophenyl)-phenylmethyl-piperazine-1-carboxylic acid-2,2,2-trichloroethylester hydrochloride

N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

Conditions
ConditionsYield
With hydrogenchloride; zinc In tetrahydrofuran; methanol at 5 - 20℃; for 1h;
With acetic acid; zinc In methanol; toluene at 41 - 45℃; for 1.41667h;
C20H20Cl4N2O2
941577-01-1

C20H20Cl4N2O2

N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

Conditions
ConditionsYield
With acetic acid; zinc In methanol for 1h;
ethyl {4-[(4-chlorophenyl)phenylmethyl]piperazin-1-yl}carboxylate
80476-89-7

ethyl {4-[(4-chlorophenyl)phenylmethyl]piperazin-1-yl}carboxylate

N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

Conditions
ConditionsYield
With potassium hydroxide In methanol for 24h; Heating;
(4-chlorophenyl)phenylmethanol
119-56-2

(4-chlorophenyl)phenylmethanol

N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: SOCl2 / CH2Cl2 / 1 h / 0 °C
2: acetonitrile / Heating
View Scheme
Multi-step reaction with 2 steps
1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 20 °C
2: acetonitrile / Reflux
View Scheme
Multi-step reaction with 2 steps
1: hydrogenchloride; calcium chloride / water / 4 h / 20 °C / Reflux
2: tetra-(n-butyl)ammonium iodide; potassium carbonate / tetrahydrofuran / 8 h / Reflux
View Scheme
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: tetrahydrofuran / 1 h / 20 °C
2: SOCl2 / CH2Cl2 / 1 h / 0 °C
3: acetonitrile / Heating
View Scheme
phenylmagnesium bromide

phenylmagnesium bromide

isopropyl magnesium halide

isopropyl magnesium halide

N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: tetrahydrofuran / 1 h / 20 °C
2: SOCl2 / CH2Cl2 / 1 h / 0 °C
3: acetonitrile / Heating
View Scheme
N-(2-hydroxyethyl)-12-bromododecanesulfonamide

N-(2-hydroxyethyl)-12-bromododecanesulfonamide

N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

Conditions
ConditionsYield
In water; N-ethyl-N,N-diisopropylamine
C24H23ClN2O2
1155402-49-5

C24H23ClN2O2

N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

Conditions
ConditionsYield
With sodium hydroxide; water In isopropyl alcohol at 90℃; for 2 - 3h; Product distribution / selectivity; Heating / reflux;
4-[(4-chloro-phenyl)-phenyl-methyl]-piperazine-1-carboxylic acid 4-nitro-phenyl ester
628717-39-5

4-[(4-chloro-phenyl)-phenyl-methyl]-piperazine-1-carboxylic acid 4-nitro-phenyl ester

N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

Conditions
ConditionsYield
With sodium hydroxide; water In isopropyl alcohol at 90℃; for 48h; Product distribution / selectivity;
4-chlorobenzophenone
134-85-0

4-chlorobenzophenone

N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium tetrahydroborate / tetrahydrofuran; methanol / 0.5 h / 0 °C
2: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 20 °C
3: acetonitrile / Reflux
View Scheme
Multi-step reaction with 3 steps
1: sodium tetrahydroborate / methanol / 1.25 h / 0 - 20 °C
2: hydrogenchloride; calcium chloride / water / 4 h / 20 °C / Reflux
3: tetra-(n-butyl)ammonium iodide; potassium carbonate / tetrahydrofuran / 8 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1.1: sodium tetrahydroborate / ethanol / 0.5 h
1.2: Cooling with ice
2.1: hydrogenchloride; calcium chloride / water / 4 h / 85 °C
3.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h
3.2: 8 h / 80 °C
View Scheme
Multi-step reaction with 3 steps
1: sodium tetrahydroborate / methanol / 20 °C
2: tetrabutylammomium bromide; hydrogenchloride / water; toluene / 40 - 45 °C
3: toluene / 60 - 100 °C
View Scheme
Multi-step reaction with 3 steps
1: sodium tetrahydroborate / methanol
2: thionyl chloride / dichloromethane / 20 °C
3: N,N-dimethyl-formamide / 80 °C
View Scheme
piperazine
110-85-0

piperazine

1-chloro-4-(chloro(phenyl)methyl)benzene
134-83-8

1-chloro-4-(chloro(phenyl)methyl)benzene

A

N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

B

1,4-bis-(4-chloro-benzhydryl)-piperazine

1,4-bis-(4-chloro-benzhydryl)-piperazine

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 85℃; Sealed tube;A n/a
B 7.6 %Chromat.
(3-bromo-3-methyl-n-butyl)benzene
52017-21-7

(3-bromo-3-methyl-n-butyl)benzene

N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

buta-1,3-diene
106-99-0

buta-1,3-diene

(E)-1-((4-chlorophenyl)(phenyl)methyl)-4-(5,5-dimethyl-7-phenylhept-2-en-1-yl)piperazine

(E)-1-((4-chlorophenyl)(phenyl)methyl)-4-(5,5-dimethyl-7-phenylhept-2-en-1-yl)piperazine

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium acetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In tetrahydrofuran; N,N-dimethyl acetamide at 20℃; for 48h; Heck Reaction; Schlenk technique; Irradiation; Inert atmosphere;99%
formaldehyd
50-00-0

formaldehyd

N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

propargyl ether mycophenolate

propargyl ether mycophenolate

mycophenoyl methyl ester-7-(butynyloxy-N-(chlorobenzhydryl)piperazine)

mycophenoyl methyl ester-7-(butynyloxy-N-(chlorobenzhydryl)piperazine)

Conditions
ConditionsYield
With copper(l) iodide In 1,4-dioxane at 120℃; for 1h;99%
2-methylthiophene-5-carboxylic acid
1918-79-2

2-methylthiophene-5-carboxylic acid

N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

1-[(4-chlorophenyl)(phenyl)methyl]-4-[(5-methyl-2-thienyl)carbonyl]piperazine

1-[(4-chlorophenyl)(phenyl)methyl]-4-[(5-methyl-2-thienyl)carbonyl]piperazine

Conditions
ConditionsYield
With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;98%
7-chloro-1-(2,4-difluorophenyl)-1,4-dihydro-8-methyl-6-nitro-4-oxoquinolone-3-carboxylic acid
1146300-32-4

7-chloro-1-(2,4-difluorophenyl)-1,4-dihydro-8-methyl-6-nitro-4-oxoquinolone-3-carboxylic acid

N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

7-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)-1-(2,4-difluorophenyl)-1,4-dihydro-8-methyl-6-nitro-4-oxoquinoline-3-carboxylic acid
1146300-51-7

7-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)-1-(2,4-difluorophenyl)-1,4-dihydro-8-methyl-6-nitro-4-oxoquinoline-3-carboxylic acid

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide Microwave irradiation;96%
N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

5-(ethoxymethylene)thiazolidine-2,4-dione

5-(ethoxymethylene)thiazolidine-2,4-dione

(Z)-5-((4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)methylene)thiazolidine-2,4-dione

(Z)-5-((4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)methylene)thiazolidine-2,4-dione

Conditions
ConditionsYield
Stage #1: N-(4-chlorobenzhydryl)piperazine; 5-(ethoxymethylene)thiazolidine-2,4-dione With triethylamine In acetonitrile
Stage #2: at 45℃;
96%
N-(3-Hydroxypropyl)-5-chloropentanesulfonamide
213774-43-7

N-(3-Hydroxypropyl)-5-chloropentanesulfonamide

chloroform methanol
7285-11-2

chloroform methanol

N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

N-(3-hydroxypropyl)-5-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]pentanesulfonamide

N-(3-hydroxypropyl)-5-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]pentanesulfonamide

Conditions
ConditionsYield
In water; N-ethyl-N,N-diisopropylamine95.1%
2-(2-chloroethoxy)acetamide
36961-64-5

2-(2-chloroethoxy)acetamide

N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

2-(2-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)ethoxy)acetamide
83881-37-2, 163837-41-0, 163837-43-2

2-(2-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)ethoxy)acetamide

Conditions
ConditionsYield
Stage #1: N-(4-chlorobenzhydryl)piperazine With tetrabutylammomium bromide; potassium carbonate In water at 25℃;
Stage #2: 2-(2-chloroethoxy)acetamide In water at 80℃;
95%
With potassium iodide; sodium chloride; sodium carbonate; sodium sulfate In di-isopropyl ether; water; toluene79.6%
N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

N-((tert-butyloxy)carbonyl)-N'-(1-(methyl)-3-(phenyl)propyl)iminodiacetic acid monoamide
737828-47-6

N-((tert-butyloxy)carbonyl)-N'-(1-(methyl)-3-(phenyl)propyl)iminodiacetic acid monoamide

(2-{4-[(4-chloro-phenyl)-phenyl-methyl]-piperazin-1-yl}-2-oxo-ethyl)-[(1-methyl-3-phenyl-propylcarbamoyl)-methyl]-carbamic acid tert-butyl ester
737828-55-6

(2-{4-[(4-chloro-phenyl)-phenyl-methyl]-piperazin-1-yl}-2-oxo-ethyl)-[(1-methyl-3-phenyl-propylcarbamoyl)-methyl]-carbamic acid tert-butyl ester

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h;94%
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h;
chloroform methanol
7285-11-2

chloroform methanol

N,N-diethyl-6-chlorohexanesulfonamide
213774-14-2

N,N-diethyl-6-chlorohexanesulfonamide

N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

N,N-Diethyl-6-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]hexanesulfonamide

N,N-Diethyl-6-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]hexanesulfonamide

Conditions
ConditionsYield
In water; N-ethyl-N,N-diisopropylamine94%
N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

chloroacetyl chloride
79-04-9

chloroacetyl chloride

2-chloro-1-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)ethanone
802009-62-7

2-chloro-1-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)ethanone

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; Inert atmosphere;94%
With triethylamine In dichloromethane at 0 - 20℃; for 7h;45%
N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

rosuvastatin
287714-41-4

rosuvastatin

(E)-7-{4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]-pyrimidin-5-yl}-(3R,5S)-3,5-dihydroxy-hept-6-enoic acid 1-[(4-chlorophenyl)-phenyl-methyl]piperazinium salt
1235588-98-3

(E)-7-{4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]-pyrimidin-5-yl}-(3R,5S)-3,5-dihydroxy-hept-6-enoic acid 1-[(4-chlorophenyl)-phenyl-methyl]piperazinium salt

Conditions
ConditionsYield
In Isopropyl acetate at 20 - 60℃; for 4.5h; Product distribution / selectivity;93%
N,N-dimethyl-6-chlorohexanesulfonamide
213774-12-0

N,N-dimethyl-6-chlorohexanesulfonamide

chloroform methanol
7285-11-2

chloroform methanol

N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

N,N-Dimethyl-6-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]hexanesulfonamide

N,N-Dimethyl-6-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]hexanesulfonamide

Conditions
ConditionsYield
In water; N-ethyl-N,N-diisopropylamine92.1%
N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

7-chloro-6-(difluoromethoxy)-1,4-dihydro-1-ethyl4-oxo-3-quinolinecarboxylic acid
115700-26-0

7-chloro-6-(difluoromethoxy)-1,4-dihydro-1-ethyl4-oxo-3-quinolinecarboxylic acid

7-{4-[(4-Chloro-phenyl)-phenyl-methyl]-piperazin-1-yl}-6-difluoromethoxy-1-ethyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

7-{4-[(4-Chloro-phenyl)-phenyl-methyl]-piperazin-1-yl}-6-difluoromethoxy-1-ethyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

Conditions
ConditionsYield
at 130 - 140℃; for 3h;92%
N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

N-((tert-butyloxy)carbonyl)-N'-(2-(4-(4-bromophenyl)thiazole))iminodiacetic acid monoamide
737828-50-1

N-((tert-butyloxy)carbonyl)-N'-(2-(4-(4-bromophenyl)thiazole))iminodiacetic acid monoamide

{[4-(4-bromo-phenyl)-thiazol-2-ylcarbamoyl]-methyl}-(2-{4-[(4-chloro-phenyl)-phenyl-methyl]-piperazin-1-yl}-2-oxo-ethyl)-carbamic acid tert-butyl ester
737828-59-0

{[4-(4-bromo-phenyl)-thiazol-2-ylcarbamoyl]-methyl}-(2-{4-[(4-chloro-phenyl)-phenyl-methyl]-piperazin-1-yl}-2-oxo-ethyl)-carbamic acid tert-butyl ester

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h;92%
ethyl 3-(o-trifluoroacetamidophenyl)-1-propargyl carbonate
889868-60-4

ethyl 3-(o-trifluoroacetamidophenyl)-1-propargyl carbonate

N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

2-{4-[(4-chloro-phenyl)-phenyl-methyl]-piperazin-1-ylmethyl}-1H-indole

2-{4-[(4-chloro-phenyl)-phenyl-methyl]-piperazin-1-ylmethyl}-1H-indole

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 80℃; for 8h;92%
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 80℃; for 8h; Inert atmosphere;92%
N-(2-Hydroxyethyl)-6-chlorohexanesulfonamide
213774-30-2

N-(2-Hydroxyethyl)-6-chlorohexanesulfonamide

chloroform methanol
7285-11-2

chloroform methanol

N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

N-(2-hydroxyethyl)-6-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]hexanesulfonamide

N-(2-hydroxyethyl)-6-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]hexanesulfonamide

Conditions
ConditionsYield
In water; N-ethyl-N,N-diisopropylamine91.5%
N-(2-Hydroxyethyl)-5-chloropentanesulfonamide
213774-42-6

N-(2-Hydroxyethyl)-5-chloropentanesulfonamide

chloroform methanol
7285-11-2

chloroform methanol

N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

N-(2-hydroxyethyl)-5-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]pentanesulfonamide

N-(2-hydroxyethyl)-5-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]pentanesulfonamide

Conditions
ConditionsYield
In water; N-ethyl-N,N-diisopropylamine91.4%
N-n-butyl-N-methyl-6-chlorohexanesulfonamide

N-n-butyl-N-methyl-6-chlorohexanesulfonamide

chloroform methanol
7285-11-2

chloroform methanol

N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

N-n-butyl-N-methyl-6-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]hexanesulfonamide

N-n-butyl-N-methyl-6-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]hexanesulfonamide

Conditions
ConditionsYield
In water; N-ethyl-N,N-diisopropylamine91.4%
N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

(2-{4-[(4-chlorophenyl)phenylmethyl]piperazin-1-yl}ethoxy)acetic acid ethyl ester

(2-{4-[(4-chlorophenyl)phenylmethyl]piperazin-1-yl}ethoxy)acetic acid ethyl ester

Conditions
ConditionsYield
With triethylamine90.8%
With triethylamine90.8%
With triethylamine In (2-chloro-ethoxy)-acetic acid ethyl ester89.4%
With triethylamine In (2-chloro-ethoxy)-acetic acid ethyl ester89.4%
N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

3-fluorobenzoyl chloride
1711-07-5

3-fluorobenzoyl chloride

{4-[(4-chlorophenyl)phenylmethyl]piperazin-1-yl}-(3-fluorophenyl)methanone

{4-[(4-chlorophenyl)phenylmethyl]piperazin-1-yl}-(3-fluorophenyl)methanone

Conditions
ConditionsYield
With dmap; triethylamine In 1,2-dichloro-ethane at 20℃;90%
7-chloro-1-cyclopropyl-1,4-dihydro-8-methyl-6-nitro-4-oxoquinolone-3-carboxylic acid
1146300-31-3

7-chloro-1-cyclopropyl-1,4-dihydro-8-methyl-6-nitro-4-oxoquinolone-3-carboxylic acid

N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

7-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)-1-cyclopropyl-1,4-dihydro-8-methyl-6-nitro-4-oxoquinoline-3-carboxylic acid
1146300-34-6

7-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)-1-cyclopropyl-1,4-dihydro-8-methyl-6-nitro-4-oxoquinoline-3-carboxylic acid

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide Microwave irradiation;90%
1-tert-butyl-7-chloro-1-1,4-dihydro-8-methyl-6-nitro-4-oxoquinolone-3-carboxylic acid
1146300-33-5

1-tert-butyl-7-chloro-1-1,4-dihydro-8-methyl-6-nitro-4-oxoquinolone-3-carboxylic acid

N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

1-tert-butyl-7-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)-1,4-dihydro-8-methyl-6-nitro-4-oxoquinoline-3-carboxylic acid
1146300-68-6

1-tert-butyl-7-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)-1,4-dihydro-8-methyl-6-nitro-4-oxoquinoline-3-carboxylic acid

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide Microwave irradiation;90%
N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

2-([(tert-butoxy)carbonyl]{2-[(4-methoxybenzyl)amino]-2-oxoethyl}amino)acetic acid
194996-03-7

2-([(tert-butoxy)carbonyl]{2-[(4-methoxybenzyl)amino]-2-oxoethyl}amino)acetic acid

N-((t-butyloxy)carbonyl)-N'-(4-methoxybenzyl)-N
737828-54-5

N-((t-butyloxy)carbonyl)-N'-(4-methoxybenzyl)-N"-1-(4-chlorobenzhydryl)piperazine iminodiacetic acid diamide

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h;89%
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h;89%
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h;
(Z)-3-(4-phenylbutan-2-ylcarbamoyl)acrylic acid
959908-92-0

(Z)-3-(4-phenylbutan-2-ylcarbamoyl)acrylic acid

N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

(Z)-4-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)-N-(4-phenylbutan-2-yl)-4-oxobut-2-enamide

(Z)-4-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)-N-(4-phenylbutan-2-yl)-4-oxobut-2-enamide

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h;89%
(2-Chloro-ethoxy)-acetic acid methyl ester
83881-47-4

(2-Chloro-ethoxy)-acetic acid methyl ester

N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

methyl 2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]-acetate
83881-46-3, 163837-44-3, 163837-46-5

methyl 2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]-acetate

Conditions
ConditionsYield
With triethylamine88.7%
With triethylamine88.7%
With potassium iodide; sodium carbonate In methanol; dichloromethane; toluene67.5%
With potassium iodide; sodium carbonate In methanol; dichloromethane; toluene55.1%
carbon disulfide
75-15-0

carbon disulfide

4-bromo-2,2-diphenylbutyronitrile
39186-58-8

4-bromo-2,2-diphenylbutyronitrile

N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

4-[(4-chloro-phenyl)-phenyl-methyl]-piperazine-1-carbodithioic acid 3-cyano-3,3-diphenyl-propyl ester

4-[(4-chloro-phenyl)-phenyl-methyl]-piperazine-1-carbodithioic acid 3-cyano-3,3-diphenyl-propyl ester

Conditions
ConditionsYield
Stage #1: carbon disulfide; N-(4-chlorobenzhydryl)piperazine With potassium phosphate In acetone at 20℃; for 0.5h;
Stage #2: 4-bromo-2,2-diphenylbutyronitrile In acetone at 20℃;
88%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

1-[(4-chlorophenyl)phenylmethyl]-4-(tert-butoxycarbonyl)-piperazine
454217-55-1, 454217-56-2, 454217-59-5

1-[(4-chlorophenyl)phenylmethyl]-4-(tert-butoxycarbonyl)-piperazine

Conditions
ConditionsYield
Stage #1: di-tert-butyl dicarbonate; N-(4-chlorobenzhydryl)piperazine With sodium hydroxide In water; toluene at 35℃; for 5h;
Stage #2: In n-heptane at 0 - 64℃; for 8.5h;
87.9%
C17H21FN2O5
1351231-59-8

C17H21FN2O5

N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

tert-butyl (S)-4-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)-1-(5-fluoroisoindolin-2-yl)-1,4-dioxobutan-2-ylcarbamate
1351231-52-1

tert-butyl (S)-4-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)-1-(5-fluoroisoindolin-2-yl)-1,4-dioxobutan-2-ylcarbamate

Conditions
ConditionsYield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In dichloromethane87%
N-(4-chlorobenzhydryl)piperazine
303-26-4

N-(4-chlorobenzhydryl)piperazine

N-((tert-butyloxy)carbonyl)-N'-(4-methylbenzyl) iminodiacetic acid monoamide
191281-21-7

N-((tert-butyloxy)carbonyl)-N'-(4-methylbenzyl) iminodiacetic acid monoamide

(2-{4-[(4-chloro-phenyl)-phenyl-methyl]-piperazin-1-yl}-2-oxo-ethyl)-[(4-methyl-benzylcarbamoyl)-methyl]-carbamic acid tert-butyl ester
737828-53-4

(2-{4-[(4-chloro-phenyl)-phenyl-methyl]-piperazin-1-yl}-2-oxo-ethyl)-[(4-methyl-benzylcarbamoyl)-methyl]-carbamic acid tert-butyl ester

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h;86%
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h;

303-26-4Relevant articles and documents

Synthesis and Anticancer Activity of 1-(1H -Indol-3-yl)-2-(4-diarylmethylpiperazine-1-yl)ethane-1,2-dione Derivatives

Jiang, Jun-Rong,Xu, Feng,Wu, Han-Gui

, (2016/08/04)

Several new 1-(4-diarylmethylpiperazine-1-yl)-2-(1H-indol-3-yl)ethane-1,2-dione derivatives were synthesized by acylation of 1-diarylmethylpiperazine with 2-(1H-indol-3-yl)-2-oxoacetyl chloride. Their structures were confirmed by 1H NMR, IR, mass spectra, and elemental analysis. These compounds were further evaluated for their anticancer activity, and most of them were found to have moderate-to-potent antiproliferative activities against Hela, A-549, and ECA-109 cancer cell lines in vitro.

Synthesis and cytotoxicity studies of novel benzhydrylpiperazine carboxamide and thioamide derivatives

Gurdal, Enise Ece,Durmaz, Irem,Cetin-Atalay, Rengul,Yarim, Mine

, p. 205 - 214 (2014/04/03)

Synthesis and cytotoxic activities of 32 benzhydrylpiperazine derivatives with carboxamide and thioamide moieties were reported. In vitro cytotoxic activities of compounds were screened against hepatocellular (HUH-7), breast (MCF-7) and colorectal (HCT-116) cancer cell lines by sulphorhodamine B assay. In general, 4-chlorobenzhydrylpiperazine derivatives were more cytotoxic than other compounds. In addition, thioamide derivatives (6a-g) have higher growth inhibition than their carboxamide analogs.

PROCASPASE-ACTIVATING COMPOUNDS AND COMPOSITIONS

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Paragraph 0088; 0207-0208, (2013/04/24)

The invention provides compounds and compositions useful for the modulation of certain enzymes. The compounds and compositions can induce of cell death, particularly cancer cell death. The invention also provides methods for the synthesis and use of the compounds and compositions, including the use of compounds and compositions in therapy for the treatment of cancer and selective induction of apoptosis in cells.

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