[ CAS No. 197638-76-9 ] {[proInfo.proName]}

Name: 197638-76-9|4-(4-Ethylpiperazin-1-yl)benzaldehyde|98%
Brand: Ambeed
SKU: A773611
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Quality Control of [ 197638-76-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 197638-76-9 ]

CAS No. :	197638-76-9	MDL No. :	MFCD05864670
Formula :	C₁₃H₁₈N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UXVDOPUAJVRFDG-UHFFFAOYSA-N
M.W :	218.29	Pubchem ID :	10513024
Synonyms :

Calculated chemistry of [ 197638-76-9 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.46
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	72.9
TPSA :	23.55 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.43 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.36
Log Po/w (XLOGP3) :	1.69
Log Po/w (WLOGP) :	0.88
Log Po/w (MLOGP) :	1.31
Log Po/w (SILICOS-IT) :	2.02
Consensus Log Po/w :	1.65

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.34
Solubility :	1.0 mg/ml ; 0.0046 mol/l
Class :	Soluble
Log S (Ali) :	-1.8
Solubility :	3.46 mg/ml ; 0.0159 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.93
Solubility :	0.258 mg/ml ; 0.00118 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.49

Safety of [ 197638-76-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 197638-76-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 197638-76-9 ]

[ 197638-76-9 ] Synthesis Path-Downstream 1~33

1
[ 111-74-0 ]
[ 197638-76-9 ]
[ 179328-89-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane for 8h; Ambient temperature;

2
[ 74-89-5 ]
[ 197638-76-9 ]
[ 197638-79-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane for 2h; Ambient temperature;

3
[ 186650-78-2 ]
[ 197638-76-9 ]

Yield	Reaction Conditions	Operation in experiment
	With diisobutylaluminium hydride In hexane; toluene at 50℃; for 1.5h;
	With diisobutylaluminium hydride In methanol; dichloromethane; water; toluene	13.C Step C Step C [4-(4-ethylpiperazinyl)benzaldehyde Under a nitrogen atmosphere, a stirred solution of 2.8 grams (0.013 mole) of 4-(4-ethyl)piperazinylbenzonitrile in 35 mL of anhydrous toluene (available from Aldrich Chemical Company) was cooled to -70° C. and 12 mL (0.02 mole) of diisobutylaluminum hydride (1.5M in toluene, available from Aldritch Chemical Company) was added dropwise at a rate to maintain the temperature below -60° C. during about a 15 minute period. Upon completion of addition, the reaction mixture was stirred at -60° C. for two hours. At the conclusion of this period, 10 mL of methanol was added dropwise followed by 10 mL of water. The resulting solution was allowed to warm to ambient temperature. Once at the prescribed temperature, 10 mL of methylene chloride was added. The resulting mixture was filtered and the filtrate was transferred to a separatory funnel. The organic layer was separated from the aqueous layer, dried with sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, yielding 1.6 grams of an orange paste. The orange pasted was was filtered through a silica gel plug. The filter cake was washed with one 75 mL portion of methylene chloride followed by one 50 mL portion of a 5% methanol/95% methylene chloride solution. The filtrate was concentrated under reduced pressure, yielding 0.5 gram of title compound. The NMR spectrum was consistent with the proposed structure.
0.5 g	Stage #1: 4-(4-ethyl-piperazin-1-yl)-benzonitrile With diisobutylaluminium hydride In toluene at -70 - -60℃; for 2.25h; Inert atmosphere; Stage #2: With water In methanol; toluene Inert atmosphere;	13.C Step C 4-(4-ethylpiperazinyl)benzaldehyde Under a nitrogen atmosphere, a stirred solution of 2.8 grams (0.013 mole) of 4-(4- ethyl)piperazinylbenzonitrile in 35 mL of anhydrous toluene (available from Aldrich Chemical Company) was cooled to -70°C and 12 mL (0.02 mole) of diisobutylaluminum hydride (1.5M in toluene, available from Aldritch Chemical Company) was added dropwise at a rate to maintain the temperature below -60°C during about a 15 minute period. Upon completion of addition, the reaction mixture was stirred at -60°C for two hours. At the conclusion of this period, 10 mL of methanol was added dropwise followed by 10 mL of water. The resulting solution was allowed to warm to ambient temperature. Once at the prescribed temperature, 10 mL of methylene chloride was added. The resulting mixture was filtered and the filtrate was transferred to a separatory funnel. The organic layer was separated from the aqueous layer, dried with sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, yielding 1.6 grams of an orange paste. The orange pasted was was filtered through a silica gel plug. The filter cake was washed with one 75 mL portion of methylene chloride followed by one 50 mL portion of a 5% methanol/95% methylene chloride solution. The filtrate was concentrated under reduced pressure, yielding 0.5 gram of title compound. The NMR spectrum was consistent with the proposed structure.

Reference： [1]Watanabe, Toshihiro; Kakefuda, Akio; Kinoyama, Isao; Takizawa, Kenji; Hirano, Seiko; Shibata, Hiroshi; Yanagisawa, Isao [Chemical and Pharmaceutical Bulletin, 1997, vol. 45, # 9, p. 1458 - 1469]
[2]Current Patent Assignee: BAYER AG - US2002/183342, 2002, A1
[3]Current Patent Assignee: BAYER AG - WO2018/202681, 2018, A1 Location in patent: Page/Page column 44; 45

4
[ 109-97-7 ]
[ 100-52-7 ]
[ 197638-76-9 ]
5-[4-(N-ethylpiperazinyl)phenyl]-10,15,20-triphenylporphine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2%	With propionic acid for 0.5h; Heating;

Reference： [1]Guo, Can-Cheng; Li, He-Ping; Zhang, Xiao-Bing [Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 8, p. 1745 - 1751]

5
[ 109-97-7 ]
[ 197638-76-9 ]
5,10,15,20-tetra-[4-(N-ethylpiperazinyl)phenyl]porphine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
4.5%	With propionic acid for 0.5h; Heating;

Reference： [1]Guo, Can-Cheng; Li, He-Ping; Zhang, Xiao-Bing [Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 8, p. 1745 - 1751]

6
[ 197638-76-9 ]
[ 197638-81-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: NaB(OAc)3H, AcOH / CH₂Cl₂ / 2 h / Ambient temperature 2: NaB(OAc)3H, AcOH / CH₂Cl₂ / 1 h / Ambient temperature

7
[ 197638-76-9 ]
[ 197638-69-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: NaB(OAc)3H, AcOH / CH₂Cl₂ / 2 h / Ambient temperature 2: NaB(OAc)3H, AcOH / CH₂Cl₂ / 1 h / Ambient temperature 3: ethanol; H₂O / 2 h / 70 °C

8
[ 197638-76-9 ]
N-Ethyl-N-(2-[4-(4-ethyl-piperazin-1-yl)-benzyl]-methyl-amino}-ethyl)-4-oxo-4-(6-oxo-5,6-dihydro-benzo[e]pyrido[3,2-b][1,4]diazepin-11-yl)-butyramide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: NaB(OAc)3H, AcOH / CH₂Cl₂ / 2 h / Ambient temperature 2: NaB(OAc)3H, AcOH / CH₂Cl₂ / 1 h / Ambient temperature 3: ethanol; H₂O / 2 h / 70 °C 4: 56 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, HOBT / dimethylformamide / 8 h / Ambient temperature

9
[ 197638-76-9 ]
N-Ethyl-N-(2-{ethyl-[4-(4-ethyl-piperazin-1-yl)-benzyl]-amino}-ethyl)-4-oxo-4-(6-oxo-5,6-dihydro-benzo[e]pyrido[3,2-b][1,4]diazepin-11-yl)-butyramide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: NaB(OAc)3H, AcOH / CH₂Cl₂ / 8 h / Ambient temperature 2: 67 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, HOBT / dimethylformamide / 8 h / Ambient temperature

10
[ 68104-63-2 ]
[ 197638-76-9 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1997,vol. 45,p. 1458 - 1469
[2]Patent: WO2018/202681,2018,A1

11
[ 5308-25-8 ]
[ 34421-94-8 ]
[ 197638-76-9 ]

Yield	Reaction Conditions	Operation in experiment
26%	Stage #1: 4-ethylpiperazine; 4-bromobenzaldehyde diethyl acetal With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 100℃; for 5h; Inert atmosphere; Stage #2: With hydrogenchloride In water; toluene for 2.5h;

Reference： [1]Bavetsias, Vassilios; Crumpler, Simon; Sun, Chongbo; Avery, Sian; Atrash, Butrus; Faisal, Amir; Moore, Andrew S.; Brown, Nathan; Sheldrake, Peter W.; Bush, Katherine; Henley, Alan; Box, Gary; Valenti, Melanie; De Haven Brandon, Alexis; Raynaud, Florence I.; Workman, Paul; Eccles, Suzanne A.; Linardopoulos, Spiros; Blagg, Julian; Kosmopoulou, Magda; Bayliss, Richard [Journal of Medicinal Chemistry, 2012, vol. 55, # 20, p. 8721 - 8734,14]

12
[ 942949-34-0 ]
[ 197638-76-9 ]
[ 1402709-64-1 ]

Yield	Reaction Conditions	Operation in experiment
15%	With sodium dithionite In ethanol; water at 80℃; for 18h; Heating;

13
[ 360-97-4 ]
[ 197638-76-9 ]
[ 1415583-49-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogensulfite; In ISOPROPYLAMIDE; at 150℃; for 1.5h;	A mixture of <strong>[360-97-4]5-aminoimidazole-4-carboxamide</strong> (6.3 gm, 0.05 moles), N-ethyl-N'-(4- formylphenyl)piperazine (10.9 gm, 0,05 moles), sodium metabisulfite (7.13 gm, 0.037 moles) and water (675mu) in dimethylacetamide (75 mL) was heated at 150C with stirring for 90 minutes. The heat was removed and water (150 mL) was cautiously added. The resulting brown solution was then cooled in an ice bath with stirring. The solid which separated was isolated by filtration, washed with water and dried. TLC (silica, 25% methanol in methylene chloride) showed the presence of two products; a bright yellow compound with rf = 0.48 and a colorless, blue fluorescent compound with rf = 0.25. The total yield was 2.4 gm.[0245] The crude product was dissolved in 20% methanol in chloroform (200 mL) and silica gel (25 gm) was added. This mixture was stripped of solvent under vacuum to give the product mixture adsorbed to silica. This material was deposited on top of a silica column (18in X 2 in). The column was then developed using 20% methanol in chloroform using 5 psi nitrogen to accelerate the process. The two compounds were cleanly separated with the yellow compound eluting first. The fractions containing the separated compounds were evaporated to give the yellow compound in a yield of 0.77 gm and the colorless compound in a yield of 0.90 gm. The NMR of the latter compound was consistent with the quinazolinone structure.

Reference： [1]Patent: WO2012/167053,2012,A1 .Location in patent: Page/Page column 88

14
[ 109-77-3 ]
[ 197638-76-9 ]
2-[4-(4-methylpiperazin-1-yl)benzylidene]malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With piperidine In ethanol at 20℃; for 1.5h;

Reference： [1]Singh, Roop Shikha; Mukhopadhyay, Sujay; Biswas, Arnab; Pandey, Daya Shankar [Chemistry - A European Journal, 2016, vol. 22, # 2, p. 753 - 763]

15
[ 5111-70-6 ]
[ 197638-76-9 ]
2-(4-(4-ethylpiperazin-1-yl)benzylidene)-5-methoxy-2,3-dihydro-1H-inden-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With potassium hydroxide In methanol at 20℃; for 48h;	4.1.1.4. 5-Methoxy, 6-methoxy or 5,6-dimethoxy-2-(4-substituedbenzilidene)-2,3-dihydro-1H-inden-1-one derivatives(15-38). General procedure: A mixture of appropriate indan-1-one derivative(2 mmol), benzaldehyde derivative (2 mmol) and potassium hydroxide(2 mmol, 0.112 g) in methanol (10 mL) was stirred at roomtemperature for 48 h. The resulting colored solid was filtered, driedand crystallized from EtOH [63].

Reference： [1]Sağlık, Begüm Nurpelin; Ilgın, Sinem; Özkay, Yusuf [European Journal of Medicinal Chemistry, 2016, vol. 124, p. 1026 - 1040]

16
[ 13623-25-1 ]
[ 197638-76-9 ]
2-(4-(4-ethylpiperazin-1-yl)benzylidene)-6-methoxy-2,3-dihydro-1H-inden-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium hydroxide In methanol at 20℃; for 48h;	4.1.1.4. 5-Methoxy, 6-methoxy or 5,6-dimethoxy-2-(4-substituedbenzilidene)-2,3-dihydro-1H-inden-1-one derivatives(15-38). General procedure: A mixture of appropriate indan-1-one derivative(2 mmol), benzaldehyde derivative (2 mmol) and potassium hydroxide(2 mmol, 0.112 g) in methanol (10 mL) was stirred at roomtemperature for 48 h. The resulting colored solid was filtered, driedand crystallized from EtOH [63].

Reference： [1]Sağlık, Begüm Nurpelin; Ilgın, Sinem; Özkay, Yusuf [European Journal of Medicinal Chemistry, 2016, vol. 124, p. 1026 - 1040]

17
[ 2107-69-9 ]
[ 197638-76-9 ]
2-(4-(4-ethylpiperazin-1-yl)benzylidene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With potassium hydroxide In methanol at 20℃; for 48h;	4.1.1.4. 5-Methoxy, 6-methoxy or 5,6-dimethoxy-2-(4-substituedbenzilidene)-2,3-dihydro-1H-inden-1-one derivatives(15-38). General procedure: A mixture of appropriate indan-1-one derivative(2 mmol), benzaldehyde derivative (2 mmol) and potassium hydroxide(2 mmol, 0.112 g) in methanol (10 mL) was stirred at roomtemperature for 48 h. The resulting colored solid was filtered, driedand crystallized from EtOH [63].

Reference： [1]Sağlık, Begüm Nurpelin; Ilgın, Sinem; Özkay, Yusuf [European Journal of Medicinal Chemistry, 2016, vol. 124, p. 1026 - 1040]

18
[ 5308-25-8 ]
[ 459-57-4 ]
[ 197638-76-9 ]

Yield	Reaction Conditions	Operation in experiment
79%	With potassium carbonate; In N,N-dimethyl-formamide;Reflux;	General procedure: A solution of 4-fluorobenzaldehyde (0.017 mol, 1.82 mL) and an appropriate secondary aminein DMF (10 mL) was refluxed (0.017 mol) in the presence of potassium carbonate (K2CO3, 0.017 mol,2.35 g). After completion of reaction, the mixture was cooled with ice-water (10 mL) and extractedwith ethyl acetate (3 20 mL). The ethyl acetate phases were combined, and the remaining productwas collected after evaporation of the solvent. The following compounds were prepared in this way:4-(4-methylpiperazin-1-yl)benzaldehyde (1a), CAS No:27913-99-1, Yield 82%, m.p. = 55-57 C (measured),m.p. = 58-60 C (reported) [60]; 4-(4-ethylpiperazin-1-yl)benzaldehyde (1b), CAS No:197638-76-9,Yield 79%, obtained as an oil; 4-(4-isopropylpiperazin-1-yl)benzaldehyde (1c), CAS No:197638-78-1,Yield 84%, obtained as an oil and 4-(4-cylopropylpiperazin-1-yl)benzaldehyde (1d), CAS No:1292778-23-4,Yield 78%, obtained as an oil.
	With potassium carbonate; In N,N-dimethyl-formamide; for 36h;Reflux;	General procedure: A mixture of 4-fluoro benzaldehyde (0.259 mL, 0.002 mol), corresponding phenol, thiophenol,or amine (0.002 mol), and a catalytic quantity of potassium carbonate (K2CO3) was refluxed in DMF(20 mL) for 36 h. After completion of the reaction, the mixture was poured into ice water (50 mL),and the precipitated product was filtered, washed with deionized water, dried, and recrystallizedfrom ethanol.

Reference： [1]Molecules,2018,vol. 23
[2]Bioorganic Chemistry,2020,vol. 97
[3]European Journal of Medicinal Chemistry,2016,vol. 124,p. 1026 - 1040
[4]Molecules,2018,vol. 23
[5]Pharmaceutical Chemistry Journal,2019,vol. 53,p. 322 - 328

19
[ 117-80-6 ]
[ 197638-76-9 ]
2-chloro-3-((4-(4-ethylpiperazin-1-yl)benzyl)amino)naphthalene-1,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.84%	Stage #1: 4-(4-ethylpiperazin-1-yl)benzaldehyde With triethylsilane; tert-butyl carbazate; trifluoroacetic acid In acetonitrile at 20℃; Inert atmosphere; Stage #2: With trifluoroacetic acid for 2h; Inert atmosphere; Stage #3: 2,3-Dichloro-1,4-naphthoquinone In ethanol Reflux; Inert atmosphere;	114 Example 114 2-chloro-3-((4-(4-ethylpiperazin-1-yl)benzyl)amino)naphthalene-1,4-dione (92) A mixture of 4-(4-ethylpiperazin-1-yl)benzaldehyde (1.50 g, 6.87 mmol), t- butylcarbamate (2.41 g, 20.61 mmol), triethylsilane (2.2 ml, 13.74 mmol) was dissolved in acetonitrile (29.3 ml) and TFA (1.05 ml). The reaction mixture was stirred at room temperature under N2 overnight. The mixture was washed with saturated (aq.) and saturated NaCl (aq.) and worked up. To the residue, TFA (4.4 ml) was added and the stirred for 2 hr. The reaction was quenched with saturated NaHCO3 (aq.) and an extraction was conducted with dichloromethane. The residue was dissolved in ethanol (10 ml) and to which 2,3-dichloro-1,4-naphthoquinone (0.95 g, 4.20 mmol) were added, and the mixture was refluxed overnight. The reaction was purified by flash column over silica gel (dichloromethane: methanol = 30: 1) to afford 92 (0.08 g, 2.84 %) as a purple solid. 1H NMR (300 MHz, CDCl3): δ 1.13 (t, J= 4.5 Hz, 3H), 2.47 (q, J= 4.5 Hz, 2H), 2.60 (t, J= 3.0 Hz, 4H), 3.23 (t, J= 3.0 Hz, 4H), 4.95 (d, J= 3.6 Hz, 2H), 6.13 (brs, 1H), 6.92 (d, J= 5.1 Hz, 2H), 7.22 (d, J= 5.1 Hz, 2H), 7.61 (t, J= 5.1 Hz, 1H), 7.72 (t, J= 5.4 Hz, 1H), 8.02 (d, J= 4.8 Hz, 1H), 8.15 (d, J= 4.8 Hz, 1H).
2.84%	Stage #1: 4-(4-ethylpiperazin-1-yl)benzaldehyde With triethylsilane; tert-butyl carbazate; trifluoroacetic acid In acetonitrile at 20℃; Inert atmosphere; Stage #2: 2,3-Dichloro-1,4-naphthoquinone In ethanol Reflux;	114 Example 114 2-chloro-3-((4-(4-ethylpiperazin-1-yl)benzyl)amino)naphthalene-1,4-dione (92) A mixture of 4-(4-ethylpiperazin-1-yl)benzaldehyde (1.50 g, 6.87 mmol), t- butylcarbamate (2.41 g, 20.61 mmol), triethylsilane (2.2 ml, 13.74 mmol) was dissolved in acetonitrile (29.3 ml) and TFA (1.05 ml). The reaction mixture was stirred at room temperature under N2overnight. The mixture was washed with saturated (aq.) and saturated NaCl (aq.) and worked up. To the residue, TFA (4.4 ml) was added and the stirred for 2 hr. The reaction was quenched with saturated NaHCO3(aq.) and an extraction was conducted with dichloromethane. The residue was dissolved in ethanol (10 ml) and to which 2,3-dichloro-1,4-naphthoquinone (0.95 g, 4.20 mmol) were added, and the mixture was refluxed overnight. The reaction was purified by flash column over silica gel (dichloromethane: methanol = 30: 1) to afford 92 (0.08 g, 2.84 %) as a purple solid.

Reference： [1]Current Patent Assignee: CALGENT BIOTECHNOLOGY - WO2017/20030, 2017, A1 Location in patent: Paragraph 00121
[2]Current Patent Assignee: TAIPEI MEDICAL UNIVERSITY - TW2018/5267, 2018, A Location in patent: Page/Page column 19; 44

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In water at 100℃; for 12h;	INTERMEDIATE 55 (0499) 4-[4-(2-Hydroxyethyl)piperazin-1-yl]benzaldehyde General procedure: To a stirred solution of 4-fluorobenzaldehyde (1.24 g, 10 mmol) in water (10 mL), 2- piperazin-1-ylethanol (1.95 g, 15 mmol) and potassium carbonate (2.76 g, 20 mmol) were added and the mixture was stirred at 100 °C for 12 h. The reaction mixture was allowed to cool down to room temperature and the formed precipitate was isolated by filtration. The filter cake was washed with water and dried in vacuum to afford 2.29 g (98%) of 99% pure title product as off-white solid.1H NMR (600 MHz, DMSO-d6) δ ppm 9.71 (s, 1 H) 7.70 (d, J=9.2 Hz, 2 H) 7.04 (d, J=9.2 Hz, 2 H) 4.44 (br. s., 1 H) 3.54 (t, J=5.6 Hz, 2 H) 3.37 (t, J=5.2 Hz, 4 H) 2.53 (t, J=5.2 Hz, 4 H) 2.43 (t, J=6.3 Hz, 2 H). MS (ESI+) m/z 235 [M+H]+ .

21
[ 10041-06-2 ]
[ 197638-76-9 ]
1-(4-(1H-imidazol-1-yl)phenyl)-3-(4-(4-ethylpiperazin-1-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With potassium hydroxide In methanol for 10h;	3.1.3. General Procedure for the Synthesis of Target Compounds (3a-3o) General procedure: 1-(4-(1H-imidazol-1-yl)phenyl)ethan-1-one (1) (0.316 g, 0.0017 mol) and appropriate 4-substitutedbenzaldehydes (2a-2o) derivatives (0.0017 mol) in methanol were stirred for 10 h in the presence ofpotassium hydroxide. The precipitated product was washed with water, dried, and recrystallizedfrom ethanol.

Reference： [1]Osmaniye, Derya; Avuşo Glu, Bet l Kaya; Sa glık, Beg m Nurpelin; Levent, Serkan; Acar evik, Ulviye; Atlı, Zlem; Zkay, Yusuf; Kaplancıklı, Zafer Asım [Molecules, 2018, vol. 23, # 4]

22
[ 30065-27-1 ]
[ 197638-76-9 ]
2-((1H-benzimidazol-2-yl)thio)-N'-(4-(4-ethylpiperazin-1-yl)benzylidene)acetohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With acetic acid; In ethanol; for 2.0h;Reflux;	General procedure: An appropriate 2-((benzazol-2-yl)thio) acetohydrazide 3a-3b (0.002 mol), and a 4-substitutedbenzaldehyde1a-1h (0.002 mol) and a catalytic amount of acetic acid were refluxed in EtOH (30 mL)for 2 h. The mixture was cooled in an ice-bath, and the precipitated product was filtered, dried andrecrystallized from EtOH.

Reference： [1]Molecules,2018,vol. 23

23
[ 24044-91-5 ]
[ 197638-76-9 ]
2-(benzothiazol-2-ylthio)-N'-(4-(4-ethylpiperazin-1-yl)benzylidene)acetohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With acetic acid In ethanol for 2h; Reflux;	3.1.4. General Procedure for the Synthesis of the Target Compounds 4a-4h General procedure: An appropriate 2-((benzazol-2-yl)thio) acetohydrazide 3a-3b (0.002 mol), and a 4-substitutedbenzaldehyde1a-1h (0.002 mol) and a catalytic amount of acetic acid were refluxed in EtOH (30 mL)for 2 h. The mixture was cooled in an ice-bath, and the precipitated product was filtered, dried andrecrystallized from EtOH.

Reference： [1]Tokgöz, Gamze; Özkay, Ümide Demir; Osmaniye, Derya; Yücel, Nazlı Turan; Can, Özgür Devrim; Kaplancıklı, Zafer Asım [Molecules, 2018, vol. 23, # 11]

24
[ 623-00-7 ]
[ 197638-76-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: 45 h / 120 °C / Inert atmosphere 2.1: triethylamine / tetrahydrofuran / 3 h / Inert atmosphere; Reflux 3.1: diisobutylaluminium hydride / toluene / 2.25 h / -70 - -60 °C / Inert atmosphere 3.2: Inert atmosphere

Reference： [1]Current Patent Assignee: BAYER AG - WO2018/202681, 2018, A1

25
[ 197638-76-9 ]
[4-(4-ethylpiperazinyl)phenyl]methan-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.3 g	With sodium tetrahydroborate; ethanol at 20℃; for 18h;	13.D Step A (4-(2-diethylamino)ethoxy)phenyl)methan-1-ol General procedure: A solution of 4.0 grams (0.08 mole) of 4-(2-(diethylamino )ethoxy )benzaldehyde (prepared in the manner of Step A, Example 3) and 2.7 grams (0.08 mole) of sodium borohydride (available from Aldrich Chemical Company) in 40 mL of methanol (available from J. T. Baker Inc,) was stirred at ambient temperature for about 18 hours. After this time, the reaction mixture was quenched with water and extracted with several portions of methylene chloride. The organic extracts were combined, dried with magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, yielding 4.1 grams of title compound.

Reference： [1]Current Patent Assignee: BAYER AG - WO2018/202681, 2018, A1 Location in patent: Page/Page column 38; 44; 45

26
[ 1131-62-0 ]
[ 197638-76-9 ]
C₂₃H₂₈N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In ethanol; water for 2h;

Reference： [1]Unsal-Tan, Oya; Tüylü Küçükkilinç, Tuba; Ayazgök, Beyza; Balkan, Ayla; Ozadali-Sari, Keriman [MedChemComm, 2019, vol. 10, # 6, p. 1018 - 1026]

27
[ 1131-62-0 ]
[ 197638-76-9 ]
1-(5-(4-(4-ethylpiperazin-1-yl)phenyl)-3-(3,4-dimethoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium hydroxide / ethanol; water / 2 h 2: hydrazine hydrate / 4 h / Reflux

Reference： [1]Unsal-Tan, Oya; Tüylü Küçükkilinç, Tuba; Ayazgök, Beyza; Balkan, Ayla; Ozadali-Sari, Keriman [MedChemComm, 2019, vol. 10, # 6, p. 1018 - 1026]

28
[ 100-06-1 ]
[ 197638-76-9 ]
1-(5-(4-(4-ethylpiperazin-1-yl)phenyl)-3-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium hydroxide / ethanol; water / 2 h 2: hydrazine hydrate / 4 h / Reflux

Reference： [1]Unsal-Tan, Oya; Tüylü Küçükkilinç, Tuba; Ayazgök, Beyza; Balkan, Ayla; Ozadali-Sari, Keriman [MedChemComm, 2019, vol. 10, # 6, p. 1018 - 1026]

29
[ 100-06-1 ]
[ 197638-76-9 ]
C₂₂H₂₆N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In ethanol; water for 2h;

Reference： [1]Unsal-Tan, Oya; Tüylü Küçükkilinç, Tuba; Ayazgök, Beyza; Balkan, Ayla; Ozadali-Sari, Keriman [MedChemComm, 2019, vol. 10, # 6, p. 1018 - 1026]

30
[ 137-07-5 ]
[ 197638-76-9 ]
2-[4-(4-ethylpiperazin-1-yl)phenyl]benzo[d]thiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	In dimethyl sulfoxide at 140℃; for 3h;

Reference： [1]Zengin, Merve; Unsal-Tan, Oya; Küçükkılınç, Tuba Tüylü; Ayazgok, Beyza; Balkan, Ayla [Pharmaceutical Chemistry Journal, 2019, vol. 53, # 4, p. 322 - 328]

31
[ 84521-15-3 ]
[ 197638-76-9 ]
(E)-5-(4-(4-ethylpiperazin-1-yl)styryl)-2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24%	Stage #1: diethyl α⁴,3-O-isopropylidene-α⁵-pyridoxylphosphonate With sodium hydride In tetrahydrofuran at 0℃; for 0.666667h; Inert atmosphere; Stage #2: 4-(4-ethylpiperazin-1-yl)benzaldehyde In tetrahydrofuran at 0℃; Inert atmosphere;	4.1.11 General procedure for the synthesis of 12b-m General procedure: To a mixture of NaH (146mg, 6.08mmol) in THF (2mL) was added a solution of intermediate 11 (500mg, 1.52mmol) in THF (4mL) at 0°C, and the mixture was stirred for 40min under argon. And a solution of corresponding substituted benzaldehydes (2-1b-m, 1.52mmol) in THF (1mL) was added dropwise. Then the mixture was stirred for another 4-7h under argon. After the reaction was completed, the mixture was quenched with 3mol/L HCl and basified with saturated aqueous solution of Na2CO3. Then the mixture was extracted with ethyl acetate (15mL×3) and the combined organic phases were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to provide crude product, the crude product was purified on silica chromatography to afford corresponding target compounds 12b-m.

Reference： [1]Cao, Zhongcheng; Deng, Yong; Li, Wei; Shi, Yichun; Song, Qing; Yang, Xia; Zhang, Li [Bioorganic Chemistry, 2020, vol. 97]

32
[ 61645-34-9 ]
[ 197638-76-9 ]
2-[2-(4-(4-ethylpiperazin-1-yl)benzylidene)hydrazinyl]quinoxaline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With acetic acid In ethanol for 1h; Reflux;	General synthesis of N-(4-substituted benzylidene)-N’-quinoxalin-2-yl-hydrazine derivatives (5a-5m) General procedure: Quinoxaline-2-hydrazine (3) (0.32 g, 2 mmol) and appropriate benzaldehyde derivatives (4a-4m) (2 mmol) in ethanol (25 mL) were refluxed for 1 h with catalytic amount of acetic acid. The precipitate was filtered, dried and recrystallized from ethanol (Kaya avuolu et al. 2018a).

Reference： [1]Ilgin, Sinem; Karaduman, Abdullah Burak; Levent, Serkan; Osmaniye, Derya; Çavuşoğlu, Betül Kaya; Çevik, Ulviye Acar; Özkay, Yusuf; Kaplancikli, Zafer Asım; Karaburun, Ahmet Çağrı; Sağlik, Begüm Nurpelin; Turan, Gülhan [Medicinal Chemistry Research, 2020, vol. 29, # 6, p. 1000 - 1011]

33
[ 934-32-7 ]
[ 197638-76-9 ]
(E)-N-(1H-benzo[d]imidazol-2-yl)-1-(4-(4-ethylpiperazin-1-yl)phenyl)methanimine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With triethylamine In ethanol at 50℃;	General procedure for the synthesis of target compounds (5a-k) General procedure: A mixture of benzaldehyde derivative 3 (1 mmol), 2-aminobenzimidazole 4 (1mmol), and triethylamine (2 mmol) in ethanol as a solvent was stirred at 50 overnight. After completion of the reaction, detected by TLC, the precipitates were collected using suction filtration and the collected solid was recrystallized in ethanol to get the pure product (5a-k).

Reference： [1]Saeedian Moghadam, Ebrahim; Al-Sadi, Abdullah Mohammed; Talebi, Meysam; Amanlou, Massoud; Amini, Mohsen; Abdel-Jalil, Raid [Synthetic Communications, 2022, vol. 52, # 1, p. 106 - 116]

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Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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[ CAS No. 197638-76-9 ] {[proInfo.proName]}

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[ 197638-76-9 ] Synthesis Path-Downstream 1~33

Related Functional Groups of [ 197638-76-9 ]

Aryls

Aldehydes

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Piperazines

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