[ CAS No. 23099-72-1 ] {[proInfo.proName]}

Name: 23099-72-1|4-Phenethylpiperazin-2-one|95%
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3d Animation Molecule Structure of 23099-72-1

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Quality Control of [ 23099-72-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 23099-72-1 ]

SDS Specification

Alternatived Products of [ 23099-72-1 ]

Product Details of [ 23099-72-1 ]

CAS No. :	23099-72-1	MDL No. :	MFCD08524856
Formula :	C₁₂H₁₆N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HZMCBPBRQHSZMM-UHFFFAOYSA-N
M.W :	204.27	Pubchem ID :	8547165
Synonyms :

Calculated chemistry of [ 23099-72-1 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.42
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	67.06
TPSA :	32.34 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.59 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.13
Log Po/w (XLOGP3) :	1.34
Log Po/w (WLOGP) :	-0.1
Log Po/w (MLOGP) :	1.18
Log Po/w (SILICOS-IT) :	1.99
Consensus Log Po/w :	1.31

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.05
Solubility :	1.83 mg/ml ; 0.00894 mol/l
Class :	Soluble
Log S (Ali) :	-1.62
Solubility :	4.89 mg/ml ; 0.0239 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.6
Solubility :	0.0515 mg/ml ; 0.000252 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.41

Safety of [ 23099-72-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 23099-72-1 ]

* 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.

Upstream synthesis route of [ 23099-72-1 ]
Downstream synthetic route of [ 23099-72-1 ]

[ 23099-72-1 ] Synthesis Path-Upstream 1~2

1
[ 5625-67-2 ]
[ 103-63-9 ]
[ 23099-72-1 ]

Yield	Reaction Conditions	Operation in experiment
74%	Stage #1: With potassium carbonate In dimethyl sulfoxide at 80℃; for 5 h; Stage #2: With hydrogenchloride In water Stage #3: With sodium hydroxide In water	A suspension of (2-bromoethyl)benzene (4.10 mL, 30.0 mmol), piperazin-2-one (3.00 g, 30.0 mmol) and K₂CO₃ (4.90 g, 36.0 mmol) in DMSO (60.0 mL) was stirred at 80° C. for 5 h. The reaction mixture was cooled to room temperature and filtered. The filtrate was then washed with water (200 mL) and extracted with methylene chloride (2). The combined organic layers were washed with brine, dried over MgSO₄, filtered, and concentrated. The result yellow solid was then dissolved in 1 N HCl (120 mL) and washed with methylene chloride. The aqueous layer was separated, basified with 6 N NaOH, and extracted with methylene chloride (3). The combined organic layers were dried over MgSO₄, filtered, and concentrated. The residue was titrated with hexanes and filtered. The filtered solid was dried under reduced pressure to give the title compound (4.50 g, 74percent) as an off-white solid: ¹H NMR (500 MHz, CDCl₃) δ 7.31-7.28 (m, 2H), 7.23-7.19 (m, 3H), 6.17 (br s, 1H), 3.40-3.37 (m, 2H), 3.23 (s, 2H), 2.83-2.79 (m, 2H), 2.73-2.67 (m, 4H).
74%	With potassium carbonate In dimethyl sulfoxide at 80℃; for 5 h;	A suspension of (2-bromoethyl)benzene (4.10 mL, 30.0 mmol), piperazin-2-one (3.00 g, 30.0 mmol) and K₂CO₃ (4.90 g, 36.0 mmol) in DMSO (60.0 mL) was stirred at 80° C. for 5 h. The reaction mixture was cooled to room temperature and filtered. The filtrate was then washed with water (200 mL) and extracted with methylene chloride (2). The combined organic layers were washed with brine, dried over MgSO₄, filtered, and concentrated. The result yellow solid was then dissolved in 1 N HCl (120 mL) and washed with methylene chloride. The aqueous layer was separated, basified with 6 N NaOH, and extracted with methylene chloride (3). The combined organic layers were dried over MgSO₄, filtered, and concentrated. The residue was titrated with hexanes and filtered. The filtered solid was dried under reduced pressure to give the title compound (4.50 g, 74percent) as an off-white solid: ¹H NMR (500 MHz, CDCl₃) δ 7.31-7.28 (m, 2H), 7.23-7.19 (m, 3H), 6.17 (brs, 1H), 3.40-3.37 (m, 2H), 3.23 (s, 2H), 2.83-2.79 (m, 2H), 2.73-2.67 (m, 4H).

Reference： [1] Patent: US2012/157460, 2012, A1, . Location in patent: Page/Page column 24
[2] Patent: US2012/157469, 2012, A1, . Location in patent: Page/Page column 18
[3] Journal of Medicinal Chemistry, 1999, vol. 42, # 18, p. 3647 - 3656

2
[ 1578249-56-5 ]
[ 23099-72-1 ]

Reference： [1] ChemPlusChem, 2014, vol. 79, # 1, p. 25 - 30

[ 23099-72-1 ] Synthesis Path-Downstream 1~2

1
[ 5625-67-2 ]
[ 103-63-9 ]
[ 23099-72-1 ]

Yield	Reaction Conditions	Operation in experiment
74%	Stage #1: 2-Ketopiperazine; 1-phenyl-2-bromoethane With potassium carbonate In dimethyl sulfoxide at 80℃; for 5h; Stage #2: With hydrogenchloride In water Stage #3: With sodium hydroxide In water	3.a A suspension of (2-bromoethyl)benzene (4.10 mL, 30.0 mmol), piperazin-2-one (3.00 g, 30.0 mmol) and K2CO3 (4.90 g, 36.0 mmol) in DMSO (60.0 mL) was stirred at 80° C. for 5 h. The reaction mixture was cooled to room temperature and filtered. The filtrate was then washed with water (200 mL) and extracted with methylene chloride (2). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The result yellow solid was then dissolved in 1 N HCl (120 mL) and washed with methylene chloride. The aqueous layer was separated, basified with 6 N NaOH, and extracted with methylene chloride (3). The combined organic layers were dried over MgSO4, filtered, and concentrated. The residue was titrated with hexanes and filtered. The filtered solid was dried under reduced pressure to give the title compound (4.50 g, 74%) as an off-white solid: 1H NMR (500 MHz, CDCl3) δ 7.31-7.28 (m, 2H), 7.23-7.19 (m, 3H), 6.17 (br s, 1H), 3.40-3.37 (m, 2H), 3.23 (s, 2H), 2.83-2.79 (m, 2H), 2.73-2.67 (m, 4H).
74%	With potassium carbonate In dimethyl sulfoxide at 80℃; for 5h;	2.e A suspension of (2-bromoethyl)benzene (4.10 mL, 30.0 mmol), piperazin-2-one (3.00 g, 30.0 mmol) and K2CO3 (4.90 g, 36.0 mmol) in DMSO (60.0 mL) was stirred at 80° C. for 5 h. The reaction mixture was cooled to room temperature and filtered. The filtrate was then washed with water (200 mL) and extracted with methylene chloride (2). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The result yellow solid was then dissolved in 1 N HCl (120 mL) and washed with methylene chloride. The aqueous layer was separated, basified with 6 N NaOH, and extracted with methylene chloride (3). The combined organic layers were dried over MgSO4, filtered, and concentrated. The residue was titrated with hexanes and filtered. The filtered solid was dried under reduced pressure to give the title compound (4.50 g, 74%) as an off-white solid: 1H NMR (500 MHz, CDCl3) δ 7.31-7.28 (m, 2H), 7.23-7.19 (m, 3H), 6.17 (brs, 1H), 3.40-3.37 (m, 2H), 3.23 (s, 2H), 2.83-2.79 (m, 2H), 2.73-2.67 (m, 4H).
67%	With potassium carbonate In N,N-dimethyl-formamide at 20℃;

Reference： [1]Current Patent Assignee: CURIA INC - US2012/157460, 2012, A1 Location in patent: Page/Page column 24
[2]Current Patent Assignee: CURIA INC - US2012/157469, 2012, A1 Location in patent: Page/Page column 18
[3]Choi, Sung-Woon; Elmaleh, David R.; Hanson, Robert N.; Fischman, Alan J. [Journal of Medicinal Chemistry, 1999, vol. 42, # 18, p. 3647 - 3656]

2
[ 1260399-96-9 ]
[ 61798-24-1 ]
[ 23099-72-1 ]
tert-butyl 5-methyl-3-(2-oxo-4-phenethylpiperazin-1-yl)-5,6,7,8,9,10-hexahydro-7,10-iminocyclohept[b]indole-11-carboxylate [ No CAS ]
1-(5-Methyl-5,6,7,8,9,10-hexahydro-7,10-iminocyclohept[b]indol-3-yl)-4-phenethylpiperazin-2-one dihydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
15%	With CuI; caesium carbonate; In 1,4-dioxane;	d) 1-(5-Methyl-5,6,7,8,9,10-hexahydro-7,10-iminocyclohept[b]indol-3-yl)-4-phenethylpiperazin-2-one dihydrochloride (Enantiomer A) (-)-tert-Butyl 3-bromo-5-methyl-5,6,7,8,9,10-hexahydro-7,10-iminocyclohept[b]indole-11-carboxylate (enantiomer A) (70.0 mg, 0.180 mmol), 4-phenethylpiperazin-2-one (40.0 mg, 0.200 mmol), CuI (69.0 mg, 0.360 mmol), trans-N,N'-dimethylcyclohexane-1,2-diamine (5.60 muL, 0.0400 mmol) and Cs2CO3 (117 mg, 0.360 mmol) in dioxane (5 mL) were reacted following the procedure for Example 2 (step c) to give tert-butyl 5-methyl-3-(2-oxo-4-phenethylpiperazin-1-yl)-5,6,7,8,9,10-hexahydro-7,10-iminocyclohept[b]indole-11-carboxylate (580 mg) as a yellow solid. The yellow solid was deprotected and converted to the hydrochloride salt according to the procedure for Example 2 (step d) to provide the title compound (12.8 mg, 15%) as a yellow solid. Free Base: 1H NMR (500 MHz, CDCl3) delta 7.47 (d, J=8.5 Hz, 1H), 7.33-7.30 (m, 2H), 7.26-7.23 (m, 3H), 7.19 (d, J=1.5 Hz, 1H), 6.96 (dd, J=8.0, 1.5 Hz, 1H), 4.70-4.69 (m, 1H), 4.21-4.40 (m, 1H), 3.76-3.73 (m, 2H), 3.44 (s, 2H), 3.43 (s, 3H), 3.42 (dd, J=16.0, 4.0 Hz, 1H), 2.92-2.86 (m, 4H), 2.77-2.74 (m, 2H), 2.56 (d, J=16.0 Hz, 1H), 2.40-2.20 (m, 2H), 2.08-2.04 (m, 1H), 1.63-1.60 (m, 1H); HPLC (Method A) 96.0% (AUC), tR=10.1 min. HCl salt: 1H NMR (500 MHz, CD3OD) delta 7.64 (d, J=8.5 Hz, 1H), 7.44 (d, J=1.5 Hz, 1H), 7.40-7.35 (m, 4H), 7.32-7.28 (m, 1H), 7.08 (dd, J=8.0, 1.5 Hz, 1H), 5.22 (d, J=5.5 Hz, 1H), 4.55-4.52 (m, 1H), 4.30-3.80 (m, 6H), 3.70 (s, 3H), 3.62-3.58 (m, 2H), 3.50 (dd, J=17.5, 4.5 Hz, 1H), 3.21-3.16 (m, 2H), 3.06 (d, J=17.0 Hz, 1H), 2.49-2.34 (m, 2H), 2.29-2.24 (m, 1H), 2.00-1.97 (m, 1H); ESI MS m/z 415 [M+H]+; HPLC (Method A) 97.8% (AUC), tR=10.0 min.

Reference： [1]Patent: US2011/3737,2011,A1

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Ghs Precautionary Statements

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
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H226	Flammable liquid and vapour
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H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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Health hazards
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H301	Toxic if swallowed
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H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
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H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 23099-72-1 ] {[proInfo.proName]}

Quality Control of [ 23099-72-1 ]

Related Doc. of [ 23099-72-1 ]

Product Details of [ 23099-72-1 ]

Calculated chemistry of [ 23099-72-1 ]

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Application In Synthesis of [ 23099-72-1 ]

[ 23099-72-1 ] Synthesis Path-Upstream 1~2

[ 23099-72-1 ] Synthesis Path-Downstream 1~2

Related Functional Groups of [ 23099-72-1 ]

Aryls

Amides

Related Parent Nucleus of [ 23099-72-1 ]

Aliphatic Heterocycles

Piperazines

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[ 23099-72-1 ]

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[ 23099-72-1 ]