[ CAS No. 225240-71-1 ] {[proInfo.proName]}

Name: 225240-71-1|Ethyl 4-methylpiperidine-4-carboxylate hydrochloride|97%
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Quality Control of [ 225240-71-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 225240-71-1 ]

Product Details of [ 225240-71-1 ]

CAS No. :	225240-71-1	MDL No. :	MFCD11045418
Formula :	C₉H₁₈ClNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZRVPAABDZYFQFB-UHFFFAOYSA-N
M.W :	207.70	Pubchem ID :	19361804
Synonyms :

Calculated chemistry of [ 225240-71-1 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.89
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	57.97
TPSA :	38.33 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) :	-6.38 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.67
Log Po/w (WLOGP) :	1.36
Log Po/w (MLOGP) :	1.31
Log Po/w (SILICOS-IT) :	1.67
Consensus Log Po/w :	1.2

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.98
Solubility :	2.17 mg/ml ; 0.0104 mol/l
Class :	Very soluble
Log S (Ali) :	-2.09
Solubility :	1.69 mg/ml ; 0.00815 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.17
Solubility :	1.4 mg/ml ; 0.00673 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.61

Safety of [ 225240-71-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 225240-71-1 ]

* 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 [ 225240-71-1 ]
Downstream synthetic route of [ 225240-71-1 ]

[ 225240-71-1 ] Synthesis Path-Upstream 1~2

1
[ 189442-87-3 ]
[ 225240-71-1 ]

Yield	Reaction Conditions	Operation in experiment
99%	With hydrogenchloride In 1,4-dioxane; ethanol at 20℃; for 6 h;	4M Solution of hydrogen chloride in 1,4-dioxane (3 mL) was added to a solution of 1- tert-butyl 4-ethyl 4-methylpiperidine-1,4-dicarboxylate (0.34 g, 1.25 mmol) in ethanol (4 mL) and the resulting mixture was stirred for 6 hours at room temperature. The solvents were evaporated and the residue was treated with diethyl ether, filtered and washed with diethyl ether to yield the hydrochloride salt of the title compound (0.3 g,99percent) as a white solid.LRMS (mlz): 172 (M+1)+.
59.6%	With hydrogenchloride In 1,4-dioxane at 0 - 20℃; for 18 h; Inert atmosphere	To a solution of Intermediate 25 ( 11.0 g, 40.5 mmol) dissolved in 1,4-Dioxane (30.0 mL) at 0-5°C was added HC1 (15.2 mL, 4 M in 1,4-dioxane) the mixture was allowed to warm to r.t. and stirred for 18h. The reaction mixture was concentrated in vacuo and residue washed with diethyl ether, yielding the title compound as an orange solid (5.02 g, 59.6percent). 1H NMR (DMSO-d₆) δ: 9.00 (m, 1 H), 4.14 (q, J 6.8 Hz, 2 H), 3.16 (m, 2 H), 2.82 (m, 2 H), 2.08 (d, J 14.4 Hz, 2 H), 1.65 (m, 2 H), 1.22 (m, 6 H).
59.6%	With hydrogenchloride In 1,4-dioxane at 0 - 20℃; for 18 h;	To a solution of Intermediate 37 (11.0 g, 40.5 mmol) dissolved in 1 ,4-dioxane (30.0 mL) at 0-5°C was added HC1 (15.2 mL, 4 M in 1,4-dioxane). The mixture was allowed to warm to r.t. and stirred for 1 8h. The reaction mixture was concentrated in vacuo and residue washed with diethyl ether, yielding the title compound as an orange solid (5.02 g, 59.6percent). 1H NMR (DMSO-d6) ö: 9.00 (m, 1 H), 4.14 (q, J 6.8 Hz, 2 H), 3.16 (m, 2 H), 2.82 (m, 2 H), 2.08 (d, J 14.4 Hz, 2 H), 1.65 (m, 2 H), 1.22 (m, 6 H).

0.90 g

With hydrogenchloride In 1,4-dioxane at 20℃; for 0.5 h;

Ethyl 4-methylpiperidine-4-carboxylate hydrochloride (ii)
To an ice-cold solution of i (1 g, 3.68 mmol) in 1,4-dioxane (10 mL) was added HCl-1,4-dioxane (4.0 M, 15 mL) solution and stirred at RT for 30 min.
The solvent was evaporated to obtain ii (0.90 g). MS: 172.16 [M+H]⁺.

Reference： [1] Patent: WO2015/86693, 2015, A1, . Location in patent: Page/Page column 121
[2] Patent: WO2015/86527, 2015, A1, . Location in patent: Page/Page column 114
[3] Patent: WO2015/86525, 2015, A1, . Location in patent: Page/Page column 117; 118
[4] Patent: WO2006/83003, 2006, A1, . Location in patent: Page/Page column 37
[5] Patent: WO2006/59945, 2006, A1, . Location in patent: Page/Page column 69
[6] Patent: US2012/88750, 2012, A1, . Location in patent: Page/Page column 17; 18
[7] Patent: US2013/252938, 2013, A1, . Location in patent: Paragraph 0466
[8] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6598 - 6603

2
[ 142851-03-4 ]
[ 225240-71-1 ]

Reference： [1] Patent: US2013/252938, 2013, A1,
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6598 - 6603
[3] Patent: WO2015/86525, 2015, A1,

[ 225240-71-1 ] Synthesis Path-Downstream 1~49

1
[ 524734-41-6 ]
[ 225240-71-1 ]
1-(8-(3-cyano-phenyl)-[1,7]naphthyridin-6-yl)-4-methyl-piperidine-4-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 70℃; for 42h;	To a solution of Compound A (360 mg, 0.96 mmol) in DMSO (3. 5 ml) under argon is added <strong>[225240-71-1]4-methyl-piperidine-4-carboxylic acid ethyl ester (hydrochloride salt)</strong> (500 mg, 2.4 mmol) and Hunig's base (0.42 ml, 3.6 mmol). The reaction mixture is stirred at 70C for 42 hours. The mixture is then allowed to cool to room temperature and partitioned between ethyl acetate and brine. The organic layer is washed twice more with brine then dried with anhydrous sodium sulfate and concentrated. Purification by flash column chromatography eluting with 9: 1 isohexane: ethyl acetate yields the desired product as an amorphous solid. MS (TOF ES+) 401.17

Reference： [1]Patent: WO2004/55013,2004,A1 .Location in patent: Page 26

2
[ 189442-87-3 ]
[ 225240-71-1 ]

Yield	Reaction Conditions	Operation in experiment
99%	With hydrogenchloride; In 1,4-dioxane; ethanol; at 20℃; for 6h;	4M Solution of hydrogen chloride in 1,4-dioxane (3 mL) was added to a solution of 1- tert-butyl 4-ethyl 4-methylpiperidine-1,4-dicarboxylate (0.34 g, 1.25 mmol) in ethanol (4 mL) and the resulting mixture was stirred for 6 hours at room temperature. The solvents were evaporated and the residue was treated with diethyl ether, filtered and washed with diethyl ether to yield the hydrochloride salt of the title compound (0.3 g,99%) as a white solid.LRMS (mlz): 172 (M+1)+.
59.6%	With hydrogenchloride; In 1,4-dioxane; at 0 - 20℃; for 18h;Inert atmosphere;	To a solution of Intermediate 25 ( 11.0 g, 40.5 mmol) dissolved in 1,4-Dioxane (30.0 mL) at 0-5C was added HC1 (15.2 mL, 4 M in 1,4-dioxane) the mixture was allowed to warm to r.t. and stirred for 18h. The reaction mixture was concentrated in vacuo and residue washed with diethyl ether, yielding the title compound as an orange solid (5.02 g, 59.6%). 1H NMR (DMSO-d6) delta: 9.00 (m, 1 H), 4.14 (q, J 6.8 Hz, 2 H), 3.16 (m, 2 H), 2.82 (m, 2 H), 2.08 (d, J 14.4 Hz, 2 H), 1.65 (m, 2 H), 1.22 (m, 6 H).
59.6%	With hydrogenchloride; In 1,4-dioxane; at 0 - 20℃; for 18h;	To a solution of Intermediate 37 (11.0 g, 40.5 mmol) dissolved in 1 ,4-dioxane (30.0 mL) at 0-5C was added HC1 (15.2 mL, 4 M in 1,4-dioxane). The mixture was allowed to warm to r.t. and stirred for 1 8h. The reaction mixture was concentrated in vacuo and residue washed with diethyl ether, yielding the title compound as an orange solid (5.02 g, 59.6%). 1H NMR (DMSO-d6) oe: 9.00 (m, 1 H), 4.14 (q, J 6.8 Hz, 2 H), 3.16 (m, 2 H), 2.82 (m, 2 H), 2.08 (d, J 14.4 Hz, 2 H), 1.65 (m, 2 H), 1.22 (m, 6 H).

	With hydrogenchloride; In dichloromethane;	Example 26; l-[6-Chloro-5-[[(tricyclo[3.3.1.13'7]dec-l-ylmethyl)amino]carbonyl]-2-quinolinyl]-4- methyl-4-piperidinecarboxylic acid; Prepared by the method of Example 3 using 2,6-dichloro-N-(tricyclo[3.3.1.13'7]dec-l- ylmethyl)-5-quinolinecarboxarnide (prepared as described in WO2003080579) and ethyl 4- methyl-piperidine-4-carboxylate hydrochloride (the product of treatment of ethyl Nu-delta°c-4- methyl-4-piperidine carboxylate (prepared as described in WO9925685) with HC1/CH2C12 and concentrating in vacuo) followed by purification by preparative HPLC to afford the 0 title compound (15 mg).1HNMR (400 MHz, d6-DMSO) delta 8.26 (IH, s), 7.86 (IH, d), 7.73 (IH, d), 7.59 (IH, d), 7.40 (IH, d), 4.08 (2H, dt), 3.53-3.43 (2H), 3.06 (2H, d), 2.09 (2H, d), 1.97 (3H, s), 1.76- 1.46 (14H, m), 1.22 (3H, s). s MS: APCI(+ve) 496 (M+H4").
	With hydrogenchloride; In 1,4-dioxane; at 20℃; for 0.5h;	To an ice-cold solution of O1-tert-butyl O4-ethyl 4-methylpiperidine-1,4-dicarboxylate (1 g, 3.68 mmol) in 1,4-dioxane (10 mL) was added HCl-1,4-dioxane (4.0 M, 15 mL) solution. The mixture was stirred at rt for 30 minutes. After completion of reaction (by TLC), solvent was evaporated to obtain brown solid material (0.90 g) that was carried forward to the next step without purification. MS: 172.16 [M+H]+.
0.90 g	With hydrogenchloride; In 1,4-dioxane; at 20℃; for 0.5h;	Ethyl 4-methylpiperidine-4-carboxylate hydrochloride (ii) To an ice-cold solution of i (1 g, 3.68 mmol) in 1,4-dioxane (10 mL) was added HCl-1,4-dioxane (4.0 M, 15 mL) solution and stirred at RT for 30 min. The solvent was evaporated to obtain ii (0.90 g). MS: 172.16 [M+H]+.

Reference： [1]Patent: WO2015/86693,2015,A1 .Location in patent: Page/Page column 121
[2]Patent: WO2015/86527,2015,A1 .Location in patent: Page/Page column 114
[3]Patent: WO2015/86525,2015,A1 .Location in patent: Page/Page column 117; 118
[4]Patent: WO2006/83003,2006,A1 .Location in patent: Page/Page column 37
[5]Patent: WO2006/59945,2006,A1 .Location in patent: Page/Page column 69
[6]Patent: US2012/88750,2012,A1 .Location in patent: Page/Page column 17; 18
[7]Patent: US2013/252938,2013,A1 .Location in patent: Paragraph 0466
[8]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 6598 - 6603

3
[ 225240-71-1 ]
[ 7379-35-3 ]
[ 905576-58-1 ]

Reference： [1]Patent: WO2006/83003,2006,A1 .Location in patent: Page/Page column 37

4
[ 37131-87-6 ]
[ 225240-71-1 ]
[ 1372547-77-7 ]

Yield	Reaction Conditions	Operation in experiment
37%		To a solution of <strong>[37131-87-6]5-bromopyrimidine-2-carboxylic acid</strong> (0.150 g, 0.742 mmol) and DMF (1 drop, catalytic amount) in DCM (10 mL) was added dropwise oxalyl chloride (0.10 mL, 1.11 mmol.) at 0 C. under inert atmosphere and the mixture stirred at rt for 1 h. The solvent was evaporated under reduced pressure under an inert atmosphere and the residue taken up in THF (5 mL) followed by the addition of DIPEA (0.70 mL, 3.71 mmol) and ethyl 4-methylpiperidine-4-carboxylate hydrochloride (0.14 g, 0.89 mmol.) at 0 C. The resulting mixture was stirred at rt for 16 h. After completion of reaction (by TLC) the mixture was poured into ice cold water (100 mL), extracted with EtOAc (3×100 mL) and the combined organics washed with water and brine, dried over Na2SO4 and filtered. The solvent was evaporated under reduced pressure and the crude residue purified on silica-gel eluting with 40% EtOAc in hexane to obtain the desired product as an off white semi-solid (0.10 g, 37% yield). MS: 358.01 [M+H]+.

Reference： [1]Patent: US2012/88750,2012,A1 .Location in patent: Page/Page column 40; 41

5
[ 225240-71-1 ]
[ 1372548-05-4 ]

Reference： [1]Patent: US2013/252938,2013,A1
[2]Patent: US2012/88750,2012,A1

6
[ 225240-71-1 ]
[ 1372547-89-1 ]

Reference： [1]Patent: US2013/252938,2013,A1
[2]Patent: US2012/88750,2012,A1

7
[ 225240-71-1 ]
[ 1372547-27-7 ]