[ CAS No. 224178-65-8 ] {[proInfo.proName]}

Name: 224178-65-8|4-(Piperidin-4-yloxy)pyridine|95%
Brand: Ambeed
SKU: A135539
Rating: 95 (29 reviews)

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Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 224178-65-8 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 224178-65-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 224178-65-8 ]

SDS Specification

Alternatived Products of [ 224178-65-8 ]

Product Details of [ 224178-65-8 ]

CAS No. :	224178-65-8	MDL No. :	MFCD14583119
Formula :	C₁₀H₁₄N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UNKDCRUEJJZIIB-UHFFFAOYSA-N
M.W :	178.23	Pubchem ID :	5152155
Synonyms :

Calculated chemistry of [ 224178-65-8 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.5
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	54.56
TPSA :	34.15 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.71 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.06
Log Po/w (XLOGP3) :	0.95
Log Po/w (WLOGP) :	0.83
Log Po/w (MLOGP) :	0.56
Log Po/w (SILICOS-IT) :	1.74
Consensus Log Po/w :	1.23

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.75
Solubility :	3.15 mg/ml ; 0.0177 mol/l
Class :	Very soluble
Log S (Ali) :	-1.25
Solubility :	9.93 mg/ml ; 0.0557 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.97
Solubility :	0.19 mg/ml ; 0.00107 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.34

Safety of [ 224178-65-8 ]

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 [ 224178-65-8 ]

* 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 [ 224178-65-8 ]
Downstream synthetic route of [ 224178-65-8 ]

[ 224178-65-8 ] Synthesis Path-Upstream 1~4

1
[ 900511-91-3 ]
[ 224178-65-8 ]

Yield	Reaction Conditions	Operation in experiment
94%	With hydrogen In methanol at 25℃; Inert atmosphere	Intermediate 2 was added to a suspension of Pd/C 10percent (1 g) MeOH (150 mL) under nitrogen atmosphere. The r.m. was stirred at 25 °C under hydrogen atmosphere. After uptake of H₂ (1 eq), the catalyst was filtered off over diatomaceous earth. The filtrate was evaporated. Yield: 2.6 g of intermediate 3 (94 percent).

Reference： [1] Patent: WO2012/126984, 2012, A1, . Location in patent: Page/Page column 34

2
[ 626-64-2 ]
[ 109384-19-2 ]
[ 224178-65-8 ]

Reference： [1] Patent: US2010/173889, 2010, A1, . Location in patent: Page/Page column 63

3
[ 4727-72-4 ]
[ 224178-65-8 ]

Reference： [1] Patent: WO2012/126984, 2012, A1,

4
[ 7379-35-3 ]
[ 224178-65-8 ]

Reference： [1] Patent: WO2012/126984, 2012, A1,

[ 224178-65-8 ] Synthesis Path-Downstream 1~16

Yield	Reaction Conditions	Operation in experiment
		Starting from (IV-6) (cf. 6.2) and 4-(piperidin-4-yloxy)-pyridine Example 1.34 can be prepared and purified analogously to Example 1.15 (cf. 15.). Analytical HPLC-MS (method B): RT=0.99 min.

2
[ 224178-65-8 ]
[ 52023-93-5 ]
[ 900511-98-0 ]

Yield	Reaction Conditions	Operation in experiment
43%	In dichloromethane; at 20℃; for 20.0h;	Preparation 34: N-(6-Methoxypyridin-3-yl)-4-(Pyridin-4-yloxy)piperidine-1-carbothioamide 5-Isothiocyanato-2-methoxypyridine [(829 mg, 4.99 mmol), J. Org. Chem. (1980), 45, 4219] was added to a solution of the product of preparation 30 (890 mg, 4.99 mmol) in dichloromethane (10 mL) and the mixture was stirred at room temperature for 20 hours. The resulting precipitate was filtered off, washing through with diethyl ether, to afford the title compound as a white solid in 43% yield, 738 mg. 1H NMR(CDCl3, 400 MHz) delta: 1.95-2.05(m, 2H), 2.06-2.15(m, 2H), 3.93-4.01(m, 5H), 4.03-4.12(m, 2H), 4.72-4.79(m, 1H), 6.75-6.85(m, 3H), 7.12(m, 1H), 7.58(m, 1H), 7.98(m, 1H), 8.40-8.44(m, 2H); LRMS APCI m/z 345 [M+H]+

Reference： [1]Patent: US2006/160786,2006,A1 .Location in patent: Page/Page column 28

3
[ 224178-65-8 ]
[ 845616-02-6 ]
(2-Isopropoxy-5-methanesulfonyl-phenyl)-[4-(pyridin-4-yloxy)-piperidin-1-yl]-methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 16.0h;	EXAMPLE 1; (2-Isopropoxy-5-methanesulfonyl-phenyl)-[4-(pyridin-4-yloxy)-piperidin-1-yl]-methanone; To a solution of 0.19 mmol 2-isopropoxy-5-methanesulfonyl-benzoic acid (Example A1) in 1 ml N,N-dimethylformamide were added successively 0.29 mmol TBTU, 0.97 mmol N-ethyldiisopropylamine and 0.19 mmol <strong>[224178-65-8]4-(piperidin-4-yloxy)-pyridine</strong>. The reaction mixture was stirred at RT for 16 h and then concentrated in vacuo. Reversed phase HPLC (acetonitrile/water) afforded the title compound as amorphous white solid (yield 75%).

Reference： [1]Patent: US2006/160788,2006,A1 .Location in patent: Page/Page column 11-12

4
[ 224178-65-8 ]
[ 1208254-84-5 ]
[ 1208254-13-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 2279 - 2282

5
[ 224178-65-8 ]
[ 123387-72-4 ]
C₁₈H₂₉N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; acetic acid; In dichloromethane; at 20℃; for 12.0h;	Stage 3: Methyl-(2-oxo-ethyl)-carbamic acid tert-butyl ester (2 equiv.), acetic acid (3 equiv.) and triacetoxy borohydride (3 equiv.) were added to a solution of the amine obtained above in dichloromethane (5 ml/mmol); the mixture was stirred for 12 hours at RT and then diluted with dichloromethane. the reaction mixture was washed with saturated sodium hydrogen carbonate solution and saturated NaCl solution, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (10% MeOH in dichloromethane).

Reference： [1]Patent: US2010/173889,2010,A1 .Location in patent: Page/Page column 63-64

6
[ 626-64-2 ]
[ 109384-19-2 ]
[ 224178-65-8 ]

Yield	Reaction Conditions	Operation in experiment
		Amine F-54: (Methyl-[2-(4-pyridin-4-yloxy-piperidin-1-yl)-ethyl]amine dihydrochlorideStage 1: N-Boc-4-hydroxy-piperidine (5.0 g, 24.8 mmol) was added at room temperature to a solution of 4-hydroxypyridine (1.89 g, 19.8 mmol) in 70 ml of dry THF. Triphenylphosphine (6.49 g, 24.77 mmol) and diisopropyl azodicarboxylate (DIAD, 4.91 ml) were added, and the reaction mixture was heated for 12 hours at 55 C. and finally concentrated under reduced pressure. 30 ml of 1M HCl were added to the residue, and the mixture was washed with dichloromethane. The combined organic phases were washed with 1M HCl and water. The combined aqueous phases were adjusted to pH 12 with 1M NaOH solution and extracted with dichloromethane. The combined organic phases were washed with saturated NaCl solution, dried over sodium sulfate and concentrated under reduced pressure. The residue was recrystallized from pentane/ether 3:1. Yield: 50%.Stage 2: 100 ml of TFA were added at 0 C. to a solution of the product obtained in stage 1 (50 g) in 400 ml of dichloromethane, and the reaction mixture was stirred for 3 hours at RT. The solvent was then distilled off, the residue was taken up in ethanol, and Amberlyst A21 resin (25 g) was added. The resin was filtered out and the solvent was removed under reduced pressure to yield the desired amine.

Reference： [1]Patent: US2010/173889,2010,A1 .Location in patent: Page/Page column 63

7
[ 224178-65-8 ]
C₂₈H₂₇F₃N₃O₈Pol [ No CAS ]
C₃₂H₃₆F₃N₄O₆Pol [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 3703 - 3707

8
[ 224178-65-8 ]
C₂₇H₂₆Cl₂N₃O₇Pol [ No CAS ]
C₃₁H₃₅Cl₂N₄O₅Pol [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 3703 - 3707

9
[ 224178-65-8 ]
[ 589-87-7 ]
[ 1187522-78-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In toluene; at 110℃; for 18.0h;	EXAMPLE 12; trans-4-{4-[4-(Piperidin-4-yloxy)piperidin-1-yl]phenyl}-3,4-dihydro-2H-quinoxaline-1-carboxylic acid (5-hydroxyadamantan-2-yl)amide (Compound No. 102); 12.1: 4-[1-(4-Bromophenyl)piperidin-4-yloxy]pyridine; 2 g of 1-bromo-4-iodobenzene and 1.386 g of <strong>[224178-65-8]4-(piperidin-4-yloxy)pyridine</strong> are placed in 35 ml of toluene and then 0.324 g of tris(dibenzylideneacetone)dipalladium(0), 0.245 g of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene and 1.019 g of sodium tert-butoxide are added. The reaction medium is heated at 110 C. for 18 h. Ethyl acetate is subsequently added and the mixture is washed twice with water and once with a saturated aqueous sodium chloride solution. The organic phase is dried over magnesium sulphate and concentrated under reduced pressure. The crude product obtained is chromatographed on silica gel, elution being carried out with a gradient of a dichloromethane/methanol (99/1 to 98/2) mixture. 1.2 g of 4-[1-(4-bromophenyl)piperidin-4-yloxy]pyridine are obtained.M+H+=335

Reference： [1]Patent: US2011/9391,2011,A1 .Location in patent: Page/Page column 39

10
[ 4727-72-4 ]
[ 224178-65-8 ]

Reference： [1]Patent: WO2012/126984,2012,A1

11
[ 7379-35-3 ]
[ 224178-65-8 ]

Reference： [1]Patent: WO2012/126984,2012,A1

12
[ 224178-65-8 ]
[ 79463-77-7 ]
[ 1400691-96-4 ]

Yield	Reaction Conditions	Operation in experiment
60%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 4h;	DIPEA (2.51 mL, 14.59 mmol) then <strong>[79463-77-7]diphenyl cyanocarbonimidate</strong> (3.58 g, 14.59 mmol) in DCM (36 mL) were added to a sol. of intermediate 3 (2.6 g, 14.59 mmol) in DCM (126 mL). The r.m. was stirred at r.t. for 4 h. Water was added and the mixture was extracted with DCM. The separated organic layer was dried (MgS04), filtered and the solvent was evaporated. The residue was purified by flash column chromatography (eluent: DCM/MeOH from 100/0 to 95/5). The product fractions were collected and concentrated in vacuo. Yield: 2.84 g of intermediate 4 (60 percent).

Reference： [1]Patent: WO2012/126984,2012,A1 .Location in patent: Page/Page column 34-35

13
[ 224178-65-8 ]
[ 1400692-12-7 ]
[ 1400692-11-6 ]

Reference： [1]Patent: WO2012/126984,2012,A1

14
[ 224178-65-8 ]
[ 1400691-81-7 ]

Reference： [1]Patent: WO2012/126984,2012,A1

15
[ 900511-91-3 ]
[ 224178-65-8 ]

Yield	Reaction Conditions	Operation in experiment
94%	With hydrogen;palladium 10% on activated carbon; In methanol; at 25℃;Inert atmosphere;	Intermediate 2 was added to a suspension of Pd/C 10% (1 g) MeOH (150 mL) under nitrogen atmosphere. The r.m. was stirred at 25 C under hydrogen atmosphere. After uptake of H2 (1 eq), the catalyst was filtered off over diatomaceous earth. The filtrate was evaporated. Yield: 2.6 g of intermediate 3 (94 %).

Reference： [1]Patent: WO2012/126984,2012,A1 .Location in patent: Page/Page column 34

16
[ 224178-65-8 ]
[ 35019-96-6 ]
N-[(1SR,2RS)-2-phenylcyclopropyl]-4-(pyridin-4-yloxy)piperidine-1-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With N-ethyl-N,N-diisopropylamine; In toluene; at 20℃; for 12.0h;	General procedure: To a solution of 4-Phenoxypiperidine (333 mg, 1.88 mmol), N,N?-diisopropylethylamine (320 mul, 1.88 mmol) in toluene (3 ml) was added trans-2-phenylcyclopropyl isocyanate (racemic) (300 mg, 1.88 mmol), and the mixture was stirred for 12 h at room temperature. The reaction mixture was then poured into water and extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2SO4 and filtrated. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (3) (309 mg, 49%) as a white solid.

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 1548 - 1557

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Ghs Precautionary Statements

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Code	Phrase
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P321
P322
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P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
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P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
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P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
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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
H223	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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H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
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
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
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. 224178-65-8 ] {[proInfo.proName]}

Quality Control of [ 224178-65-8 ]

Related Doc. of [ 224178-65-8 ]

Product Details of [ 224178-65-8 ]

Calculated chemistry of [ 224178-65-8 ]

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 224178-65-8 ]

Application In Synthesis of [ 224178-65-8 ]

[ 224178-65-8 ] Synthesis Path-Upstream 1~4

[ 224178-65-8 ] Synthesis Path-Downstream 1~16

Related Functional Groups of [ 224178-65-8 ]

Ethers

Related Parent Nucleus of [ 224178-65-8 ]

Pyridines

Piperidines

Precautionary Statements-General

Prevention

Response

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Physical hazards

Health hazards

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[ 224178-65-8 ]

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[ 224178-65-8 ]