27469-61-0

Basic information

• Product Name: 1-(4,4'-DICHLOROBENZHYDRYL)PIPERAZINE
• Synonyms: 1-(4,4'-DICHLOROBENZHYDRYL)PIPERAZINE;Dichlorobenzhydrylpiperazine;1-(4,4Dichlorbenzhydryl)piperazine;1-(4,4'-Dichlorobenzhydryl)piperazine 98%;1-(4,4'-Dichlorobenzhydryl)piperazine98%
• CAS NO: 27469-61-0
• Molecular Formula: C₁₇H₁₈Cl₂N₂
• Molecular Weight: 321.24
• Mol File: 27469-61-0.mol
• Article Data: 9

Chemical Properties

• Melting Point: 107 °C
• Boiling Point: 425.4 °C at 760 mmHg
• Flash Point: 211.1 °C
• Appearance: /
• Density: 1.237 g/cm³
• Vapor Pressure: 1.91E-07mmHg at 25°C
• Refractive Index: 1.599
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 8.97±0.10(Predicted)
• CAS DataBase Reference: 1-(4,4'-DICHLOROBENZHYDRYL)PIPERAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4,4'-DICHLOROBENZHYDRYL)PIPERAZINE(27469-61-0)
• EPA Substance Registry System: 1-(4,4'-DICHLOROBENZHYDRYL)PIPERAZINE(27469-61-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 27469-61-0(Hazardous Substances Data)

Usage

General Description

1-(4,4'-Dichlorobenzhydryl)piperazine is a synthetic organic compound that consists of a piperazine ring substituted with a 4,4'-dichlorobenzhydryl group. It's primarily known for its role as a chemical intermediate in the production of pharmaceuticals and other synthetic compounds. The compound could be of significant interest in various research and industrial contexts due to its benzhydryl group and dichloro substitution. However, like many chemicals, it should be handled and stored properly to avoid risks associated with exposure or environmentally unsustainable disposal procedures.

InChI:InChI=1/C17H18Cl2N2/c18-15-5-1-13(2-6-15)17(21-11-9-20-10-12-21)14-3-7-16(19)8-4-14/h1-8,17,20H,9-12H2

Synthetic route

ethyl <4-(bis (4-chlorophenyl) methyl)-1-piperazinyl> carboxylate (154544-61-3) → 1-(4,4'-dichloro-benzhydryl)-piperazine (27469-61-0)

Conditions	Yield
With sodium hydroxide In methanol for 72h; Heating;	96%

(4-chlorophenyl)phenylmethanol (119-56-2) → 1-(4,4'-dichloro-benzhydryl)-piperazine (27469-61-0)

Conditions	Yield
In dichloromethane	88.4%
In dichloromethane	88.4%
In dichloromethane	88.4%
In dichloromethane	88.4%
In dichloromethane	88.4%

piperazine (110-85-0) + chlorobis(4-chlorophenyl)methane (782-08-1) → 1-(4,4'-dichloro-benzhydryl)-piperazine (27469-61-0)

Conditions	Yield
In acetonitrile at 90℃; for 16h;	74%
In acetonitrile Reflux;	68%
In acetonitrile for 2h; Heating;	60%

4,4'-dichlorobenzophenone (90-97-1) → 1-(4,4'-dichloro-benzhydryl)-piperazine (27469-61-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 98 percent / SOCl2 / cyclohexane / 24 h / Heating 2: 19 percent / K2CO3 / tetrahydrofuran / 14 h / Heating 3: 96 percent / 10percent aq. NaOH / methanol / 72 h / Heating View Scheme
Multi-step reaction with 2 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 20 °C 2: acetonitrile / Reflux View Scheme

chlorobis(4-chlorophenyl)methane (782-08-1) → 1-(4,4'-dichloro-benzhydryl)-piperazine (27469-61-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 19 percent / K2CO3 / tetrahydrofuran / 14 h / Heating 2: 96 percent / 10percent aq. NaOH / methanol / 72 h / Heating View Scheme

4,4'-Dichlorobenzophenone (90-98-2) → 1-(4,4'-dichloro-benzhydryl)-piperazine (27469-61-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: NaBH4 / methanol 2: 98 percent / SOCl2 / cyclohexane / 24 h / Heating 3: 19 percent / K2CO3 / tetrahydrofuran / 14 h / Heating 4: 96 percent / 10percent aq. NaOH / methanol / 72 h / Heating View Scheme
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

2-chloronicotinic acid (2942-59-8) + 1-(4,4'-dichloro-benzhydryl)-piperazine (27469-61-0) → (4-(bis(4-chlorophenyl)methyl)piperazin-1-yl)(2-chloropyridin-3-yl)methanone

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	99%

2-chloroisonicotinic acid, (6313-54-8) + 1-(4,4'-dichloro-benzhydryl)-piperazine (27469-61-0) → (4-(bis(4-chlorophenyl)methyl)piperazin-1-yl)(2-chloropyridin-4-yl)methanone

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	98%

N-(2-Hydroxyethyl)-5-chloropentanesulfonamide (213774-42-6) + chloroform methanol (7285-11-2) + 1-(4,4'-dichloro-benzhydryl)-piperazine (27469-61-0) → N-(2-hydroxyethyl)-5-[4-[bis(4-chlorophenyl)methyl]-1-piperazinyl]pentanesulfonamide

Conditions	Yield
In water; N-ethyl-N,N-diisopropylamine	97.5%

1-(4,4'-dichloro-benzhydryl)-piperazine (27469-61-0) + 2,5‐difluoro‐4‐nitrobenzoic acid (116465-48-6) → (4-(bis(4-chlorophenyl)methyl)piperazin-1-yl)(2,5-difluoro-4-nitrophenyl)methanone

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	96%

N-(2-Hydroxyethyl)-6-chlorohexanesulfonamide (213774-30-2) + chloroform methanol (7285-11-2) + 1-(4,4'-dichloro-benzhydryl)-piperazine (27469-61-0) → N-(2-hydroxyethyl)-6-[4-[bis(4-chlorophenyl)methyl]-1-piperazinyl]hexanesulfonamide

Conditions	Yield
In water; N-ethyl-N,N-diisopropylamine	92.2%

2-ethynyl-thiophene (4298-52-6) + formaldehyd (50-00-0) + 1-(4,4'-dichloro-benzhydryl)-piperazine (27469-61-0) → 1--4-<3-(2-thienyl)-2-propynyl>piperazine (105314-56-5)

Conditions	Yield
copper(II) sulfate In tetrahydrofuran for 5.75h; Heating;	91%

2,5-difluorobenzoyl chloride (35730-09-7) + 1-(4,4'-dichloro-benzhydryl)-piperazine (27469-61-0) → {4-[bis-(4-chlorophenyl)-methyl]piperazin-1-yl}-(2,5-difluorophenyl)methanone

Conditions	Yield
With dmap; triethylamine In 1,2-dichloro-ethane at 20℃;	90%

1-(4,4'-dichloro-benzhydryl)-piperazine (27469-61-0) + 4-fluorobenzoyl chloride (403-43-0) → {4-[bis-(4-chlorophenyl)methyl]piperazin-1-yl}-(4-fluorophenyl)methanone

Conditions	Yield
With dmap; triethylamine In 1,2-dichloro-ethane at 20℃;	90%

1-(4,4'-dichloro-benzhydryl)-piperazine (27469-61-0) + 3-fluorobenzoyl chloride (1711-07-5) → {4-[bis-(4-chlorophenyl)methyl]piperazin-1-yl}-(3-fluorophenyl)methanone

Conditions	Yield
With dmap; triethylamine In 1,2-dichloro-ethane at 20℃;	90%

1-(4,4'-dichloro-benzhydryl)-piperazine (27469-61-0) + 2-Fluorobenzoyl chloride (393-52-2) → {4-[bis-(4-chlorophenyl)methyl]piperazin-1-yl}-(2-fluorophenyl)methanone

Conditions	Yield
With dmap; triethylamine In 1,2-dichloro-ethane at 20℃;	90%

[3-(diphenylmethyl)-2-oxo-2,3-dihydro-1H-imidazol-1-yl]acetic acid + 1-(4,4'-dichloro-benzhydryl)-piperazine (27469-61-0) → 1-benzhydryl-3-(2-{4-[bis-(4-chlorophenyl)methyl]piperazin-1-yl}-2-oxoethyl)imidazolidin-2-one

Conditions	Yield
Stage #1: [3-(diphenylmethyl)-2-oxo-2,3-dihydro-1H-imidazol-1-yl]acetic acid; 1-(4,4'-dichloro-benzhydryl)-piperazine With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 5h; Stage #2: With sodium hydrogencarbonate In dichloromethane; water	89%

1-(4,4'-dichloro-benzhydryl)-piperazine (27469-61-0) + Cyclobutanecarbonyl chloride (5006-22-4) → {4-[bis-(4-chlorophenyl)methyl]piperazin-1-yl}cyclobutylmethanone

Conditions	Yield
With dmap; triethylamine In 1,2-dichloro-ethane at 20℃;	88%

1-(4,4'-dichloro-benzhydryl)-piperazine (27469-61-0) + n-valeryl chloride (638-29-9) → 1-{4-[bis-(4-chlorophenyl)methyl]piperazin-1-yl}pentan-1-one

Conditions	Yield
With dmap; triethylamine In 1,2-dichloro-ethane at 20℃;	85%

2-Butynoic acid (590-93-2) + 1-(4,4'-dichloro-benzhydryl)-piperazine (27469-61-0) → 1-(4-(bis(4-chlorophenyl)methyl)piperazin-1-yl)but-2-yn-1-one

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h;	82%

1-(4,4'-dichloro-benzhydryl)-piperazine (27469-61-0) + 3-(Trifluoromethyl)benzoyl chloride (2251-65-2) → {4-[bis-(4-chlorophenyl)methyl]piperazin-1-yl}-(3-trifluoromethylphenyl)methanone

Conditions	Yield
With dmap; triethylamine In 1,2-dichloro-ethane at 20℃;	81%

1-(4,4'-dichloro-benzhydryl)-piperazine (27469-61-0) + Propiolic acid (471-25-0) → 1-(4-(bis(4-chlorophenyl)methyl)piperazin-1-yl)prop-2-yn-1-one

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h;	81%

2-Chloronicotinoyl chloride (49609-84-9) + 1-(4,4'-dichloro-benzhydryl)-piperazine (27469-61-0) → (4-(bis(4-chlorophenyl)methyl)piperazin-1-yl)(2-chloropyridin-3-yl)methanone

Conditions	Yield
With dmap; triethylamine In 1,2-dichloro-ethane at 20℃;	79%

5-methyl-4-nitroisoxazole-3-carbonyl chloride + 1-(4,4'-dichloro-benzhydryl)-piperazine (27469-61-0) → (4-(bis(4-chlorophenyl)methyl)piperazin-1-yl)(5-methyl-4-nitroisoxazol-3-yl)methanone (1360705-96-9)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 2h;	74%

3-(trimethylsilyl)prop-2-ynoic acid (5683-31-8) + 1-(4,4'-dichloro-benzhydryl)-piperazine (27469-61-0) → 1-(4-(bis(4-chlorophenyl)methyl)piperazin-1-yl)-3-(trimethylsilyl)prop-2-yn-1-one

Conditions	Yield
With dicyclohexyl-carbodiimide at 20℃; for 1h;	74%

1-(4,4'-dichloro-benzhydryl)-piperazine (27469-61-0) + 1-bromo-3-phenylprop-2-yne (1794-48-5) → 1--4-(3-phenyl-2-propynyl)piperazine (137242-74-1)

Conditions	Yield
With sodium carbonate; potassium iodide In toluene for 1.5h;	72%

3,5-bis(trifluoromethyl)phenyl carboxylic acid chloride (785-56-8) + 1-(4,4'-dichloro-benzhydryl)-piperazine (27469-61-0) → {4-[bis-(4-chlorophenyl)methyl]piperazin-1-yl}-(3,5-ditrifluoromethylphenyl)methanone

Conditions	Yield
With dmap; triethylamine In 1,2-dichloro-ethane at 20℃;	72%

1-(4,4'-dichloro-benzhydryl)-piperazine (27469-61-0) + benzyl chloroformate (501-53-1) → benzyl 4-(bis(4-chlorophenyl)methyl)piperazine-1-carboxylate (1028991-80-1)

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	70%

1-(4,4'-dichloro-benzhydryl)-piperazine (27469-61-0) + 2-chloro-3-nitrobezoic acid (3970-35-2) → (4-(bis(4-chlorophenyl)methyl)piperazin-1-yl)(2-chloro-3-nitrophenyl)methanone

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	64%

(E)-but-2-enoic acid (107-93-7) + 1-(4,4'-dichloro-benzhydryl)-piperazine (27469-61-0) → (E)-1-(4-(bis(4-chlorophenyl)methyl)piperazin-1-yl)but-2-en-1-one

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	63%

1-(4,4'-dichloro-benzhydryl)-piperazine (27469-61-0) + Cyclohexanecarboxylic acid (98-89-5) → C24H28Cl2N2O (1028991-49-2)

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃;	62%

bis(trichloromethyl) carbonate (32315-10-9) + 1-(4,4'-dichloro-benzhydryl)-piperazine (27469-61-0) + methyl d,l-2-hydroxy-3,3,3-trifluoropropionate (93496-85-6) → 1,1,1-trifluoro-3-methoxy-3-oxopropan-2-yl 4-(bis(4-chlorophenyl)methyl)piperazine-1-carboxylate (1446817-38-4)

Conditions	Yield
Stage #1: bis(trichloromethyl) carbonate; methyl d,l-2-hydroxy-3,3,3-trifluoropropionate With N-ethyl-N,N-diisopropylamine In dichloromethane for 2h; Stage #2: 1-(4,4'-dichloro-benzhydryl)-piperazine In dichloromethane for 2h;	62%

2-fluoro-5-nitrobenzoic acid (7304-32-7) + 1-(4,4'-dichloro-benzhydryl)-piperazine (27469-61-0) → (4-(bis(4-chlorophenyl)methyl)piperazin-1-yl)(2-fluoro-5-nitrophenyl)methanone

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	59%

Upstream product

• 110-85-0 piperazine 
• 782-08-1 chlorobis(4-chlorophenyl)methane 
• 90-98-2 4,4'-Dichlorobenzophenone 
• 119-56-2 (4-chlorophenyl)phenylmethanol 
• 90-97-1 4,4'-dichlorobenzophenone 
• 154544-61-3 ethyl <4-(bis (4-chlorophenyl) methyl)-1-piperazinyl> carboxylate 

Downstream Products

• 105314-56-5 1--4-<3-(2-thienyl)-2-propynyl>piperazine 
• 118419-78-6 4-{4-[Bis-(4-chloro-phenyl)-methyl]-piperazin-1-yl}-butylamine 
• 125345-86-0 1-(1-Chloro-2-hydroxy-3-propanyl)-4-[bis(4-chlorophenyl)methyl]piperazine 

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