[ CAS No. 32188-75-3 ] {[proInfo.proName]}

Name: 32188-75-3|5-Nitro-2-(piperidin-1-yl)benzonitrile|95%
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SKU: A128951
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Quality Control of [ 32188-75-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 32188-75-3 ]

SDS Specification

Alternatived Products of [ 32188-75-3 ]

Product Details of [ 32188-75-3 ]

CAS No. :	32188-75-3	MDL No. :	MFCD05365582
Formula :	C₁₂H₁₃N₃O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AFQKJSKHZCXGLQ-UHFFFAOYSA-N
M.W :	231.25	Pubchem ID :	4811199
Synonyms :

Calculated chemistry of [ 32188-75-3 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.42
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	69.43
TPSA :	72.85 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.98 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.84
Log Po/w (XLOGP3) :	2.44
Log Po/w (WLOGP) :	2.08
Log Po/w (MLOGP) :	0.83
Log Po/w (SILICOS-IT) :	0.31
Consensus Log Po/w :	1.5

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.94
Solubility :	0.265 mg/ml ; 0.00115 mol/l
Class :	Soluble
Log S (Ali) :	-3.61
Solubility :	0.0564 mg/ml ; 0.000244 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.6
Solubility :	0.586 mg/ml ; 0.00254 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	1.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.11

Safety of [ 32188-75-3 ]

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 [ 32188-75-3 ]

* 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 [ 32188-75-3 ]
Downstream synthetic route of [ 32188-75-3 ]

[ 32188-75-3 ] Synthesis Path-Upstream 1~7

1
[ 32188-75-3 ]
[ 34595-33-0 ]

Yield	Reaction Conditions	Operation in experiment
92%	for 0.5 h;	The compound 5-nitro-2- (piperidin-1-yl) benzoic acid was subjected to reduction reaction by NaBH4 for 30 min, followed by 2.0 g of a yellow solid (Compound 11)
87%	With hydrogen In methanol for 16 h;	Step 2; 2-(1-piperidinyl)-5-(amino)benzonitrile; The 2-(1-piperidinyl)-5-(nitro)benzonitrile (25 g, 108 mmol) was solubilized in methanol (400 ml). A spatula tip of Pd/C was added to the mixture and the crude was stirred for 16 hours under hydrogen atmosphere. The mixture was filtered on Celite.(R)., concentrated and the expected product was isolated by recrystallization in an equimolar volume of dichloromethane and cyclohexane. Yield: 87percent

Reference： [1] Patent: CN106892871, 2017, A, . Location in patent: Paragraph 0135; 0138; 0139
[2] Patent: US2006/79696, 2006, A1, . Location in patent: Page/Page column 38
[3] Patent: EP1176140, 2002, A1, . Location in patent: Page 54

2
[ 32188-75-3 ]
[ 7439-89-6 ]
[ 34595-33-0 ]

Reference： [1] Patent: US2003/203909, 2003, A1,

3
[ 110-89-4 ]
[ 16588-02-6 ]
[ 32188-75-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 3 h;	A mixture of 2-chloro-5-nitrobenzonitrile (2g,1 eq,10.96mmol), potassium carbonate (4.54g, 3eq, 32.7001), piperidine (1 · 63 mL, 1.5 eq, 16.34 mmol) and DMF (5 mL) at 90 ° C Should be 3h, until the reaction is complete, remove the oil bath. DMF was diluted with 100 mL EA, washed with saturated ammonium chloride and sodium chloride respectively. The aqueous phase was extracted again with ethyl acetate. The organic phases were combined and dried over anhydrous sodium sulfate. The filtrate was concentrated to give a yellow solid (Compound 10) 2.528 g, yield 99percent

Reference： [1] Patent: CN106892871, 2017, A, . Location in patent: Paragraph 0135-0137
[2] Patent: US2003/203909, 2003, A1,
[3] European Journal of Organic Chemistry, 2007, # 8, p. 1378 - 1383
[4] Patent: EP1176140, 2002, A1, . Location in patent: Page 53

4
[ 16588-15-1 ]
[ 32188-75-3 ]

Reference： [1] Patent: EP1176140, 2002, A1,

5
[ 2516-96-3 ]
[ 32188-75-3 ]

Reference： [1] Patent: EP1176140, 2002, A1,

6
[ 110-89-4 ]
[ 17417-09-3 ]
[ 32188-75-3 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1994, # 3, p. 443 - 450
[2] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1994, # 3, p. 443 - 450
[3] Journal of the Chemical Society. Perkin Transactions 2, 1998, # 4, p. 937 - 942

7
[ 110-89-4 ]
[ 63707-35-7 ]
[ 32188-75-3 ]

[ 32188-75-3 ] Synthesis Path-Downstream 1~18

1
[ 110-89-4 ]
[ 17417-09-3 ]
[ 32188-75-3 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1994,p. 443 - 450
[2]Journal of the Chemical Society. Perkin transactions II,1994,p. 443 - 450
[3]Journal of the Chemical Society. Perkin Transactions 2 (2001),1998,p. 937 - 942

2
[ 110-89-4 ]
[ 63707-35-7 ]
[ 32188-75-3 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1994,p. 443 - 450
[2]Journal of the Chemical Society. Perkin transactions II,1994,p. 443 - 450

3
[ 32188-75-3 ]
[ 143675-92-7 ]
[ 50891-30-0 ]

Reference： [1]Pharmazie,1992,vol. 47,p. 243 - 245

4
[ 32188-75-3 ]
[ 50891-30-0 ]

Reference： [1]Pharmazie,1992,vol. 47,p. 243 - 245

6
[ 32188-75-3 ]
[ 143675-98-3 ]

Reference： [1]Pharmazie,1992,vol. 47,p. 243 - 245
[2]Pharmazie,1992,vol. 47,p. 243 - 245

7
[ 110-89-4 ]
[ 16588-02-6 ]
[ 32188-75-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium carbonate; In N,N-dimethyl-formamide; at 90.0℃; for 3.0h;	A mixture of 2-chloro-5-nitrobenzonitrile (2g,1 eq,10.96mmol), potassium carbonate (4.54g, 3eq, 32.7001), piperidine (1 · 63 mL, 1.5 eq, 16.34 mmol) and DMF (5 mL) at 90 C Should be 3h, until the reaction is complete, remove the oil bath. DMF was diluted with 100 mL EA, washed with saturated ammonium chloride and sodium chloride respectively. The aqueous phase was extracted again with ethyl acetate. The organic phases were combined and dried over anhydrous sodium sulfate. The filtrate was concentrated to give a yellow solid (Compound 10) 2.528 g, yield 99%
	In di-isopropyl ether; acetonitrile;	STARTING MATERIAL SYNTHETIC EXAMPLE 4 5-amino-2-piperidinobenzonitrile 2-Chloro-5-nitrobenzonitrile (20 g) and piperidine (9.34 g) were added to acetonitrile (100 ml) and the mixture was stirred at the refluxing temperature for 1 hr. The solvent was evaporated under reduced pressure. Diisopropyl ether was added to the residue to allow crystallization and the crystals were recrystallized from methanol to give 5-nitro-2-piperidinobenzonitrile (17 g).

Reference： [1]Patent: CN106892871,2017,A .Location in patent: Paragraph 0135-0137
[2]Patent: US2003/203909,2003,A1
[3]European Journal of Organic Chemistry,2007,p. 1378 - 1383
[4]Patent: EP1176140,2002,A1 .Location in patent: Page 53

8
[ 32188-75-3 ]
[ 34595-33-0 ]

Yield	Reaction Conditions	Operation in experiment
92%	With sodium tetrahydroborate; for 0.5h;	The compound 5-nitro-2- (piperidin-1-yl) benzoic acid was subjected to reduction reaction by NaBH4 for 30 min, followed by 2.0 g of a yellow solid (Compound 11)
87%	With hydrogen;palladium over charcoal; In methanol; for 16.0h;	Step 2; 2-(1-piperidinyl)-5-(amino)benzonitrile; The 2-(1-piperidinyl)-5-(nitro)benzonitrile (25 g, 108 mmol) was solubilized in methanol (400 ml). A spatula tip of Pd/C was added to the mixture and the crude was stirred for 16 hours under hydrogen atmosphere. The mixture was filtered on Celite, concentrated and the expected product was isolated by recrystallization in an equimolar volume of dichloromethane and cyclohexane. Yield: 87%

Reference： [1]Patent: CN106892871,2017,A .Location in patent: Paragraph 0135; 0138; 0139
[2]Patent: US2006/79696,2006,A1 .Location in patent: Page/Page column 38
[3]Patent: EP1176140,2002,A1 .Location in patent: Page 54

9
[ 32188-75-3 ]
[ 7439-89-6 ]
[ 34595-33-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; ammonium chloride; In ethanol; di-isopropyl ether; water;	Subsequently, ammonium chloride (1.6 g) and iron powder (8.4 g) were added to a mixed solvent of water (40 ml) and ethanol (120 ml) and the mixture was heated to 65 C. 5-Nitro-2-piperidinobenzonitrile (10 g) was added by portions over 20 min and the mixture was stirred at the refluxing temperature for 30 min. The reaction mixture was ice-cooled and the reaction solution was filtrated. The solvent was evaporated under reduced pressure. An aqueous sodium hydroxide solution was added and the mixture was extracted with toluene. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. Diisopropyl ether was added to the residue to allow crystallization and the crystals were recrystallized from a mixed solvent of ethyl acetate-n-hexane to give the title compound (8.3 g). melting point: 148-149 C. 1H-NMR (270 MHz, CDCl3)delta(ppm):1.50-1.59 (2H, m), 1.71-1.79 (4H, m), 2.96-3.04 (4H, m), 3.6 (2H, brs), 6.76-6.90 (3H, m).

Reference： [1]Patent: US2003/203909,2003,A1

10
[ 16588-15-1 ]
[ 32188-75-3 ]