[ CAS No. 146093-46-1 ] {[proInfo.proName]}

Name: 146093-46-1|4-(Aminoethyl)-1-N-Boc-piperidine|95%
Brand: Ambeed
SKU: A186462
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Quality Control of [ 146093-46-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 146093-46-1 ]

Product Details of [ 146093-46-1 ]

CAS No. :	146093-46-1	MDL No. :	MFCD04038459
Formula :	C₁₂H₂₄N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LBQDLHPFISVBRU-UHFFFAOYSA-N
M.W :	228.33	Pubchem ID :	1514258
Synonyms :

Calculated chemistry of [ 146093-46-1 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.92
Num. rotatable bonds :	5
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	68.91
TPSA :	55.56 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) :	-6.79 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.83
Log Po/w (XLOGP3) :	1.27
Log Po/w (WLOGP) :	1.6
Log Po/w (MLOGP) :	1.44
Log Po/w (SILICOS-IT) :	1.07
Consensus Log Po/w :	1.64

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.73
Solubility :	4.29 mg/ml ; 0.0188 mol/l
Class :	Very soluble
Log S (Ali) :	-2.04
Solubility :	2.1 mg/ml ; 0.00921 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.73
Solubility :	4.23 mg/ml ; 0.0185 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.21

Safety of [ 146093-46-1 ]

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 [ 146093-46-1 ]

* 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 [ 146093-46-1 ]
Downstream synthetic route of [ 146093-46-1 ]

[ 146093-46-1 ] Synthesis Path-Upstream 1~12

1
[ 256411-39-9 ]
[ 146093-46-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	With ammonium hydroxide; hydrogen In methanol at 50℃; for 5 h;	A mixture of tert-butyl 4-(cyanomethyl)piperidine-1-carboxylate (20 g, 89.29 mmol) and NH₄OH (9 mL) in MeOH (200 mL) was hydrogenated with Raney Ni (6 g, 101.69 mmol) at 50°C for 5 h under 50 psi of H₂. The mixture was filtered through a celite pad and the filtrate was concentrated to afford product (20.5 g, 100percent) as colorless oil. ¹H NMR (400 MHz, CDCl₃) δ 1.06 - 1.19 (m, 2H) 1.44 (d, J=7.41 Hz, 2H) 1.47 (s, 9H) 1.50 - 1.58 (m, 1H) 1.66 (d, J=12.49 Hz, 2H) 2.09 (br. s., 2H) 2.70 (t, J=12.29 Hz, 2H) 2.75 - 2.83 (m, 2H) 4.08 (br. s., 2H).

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 21, p. 4805 - 4811

2
[ 150022-51-8 ]
[ 146093-46-1 ]

Yield	Reaction Conditions	Operation in experiment
78%	at 20℃; for 5.5 h;	5.5 g (15.34 mmol) of tert-butyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethyl)piperidine-1-carboxylate prepared previously are solubilized in 40 ml of ethanol amine and the mixture is stirred at room temperature for 5.5 h. Then it is poured into 150 ml of water and extracted twice with 200 ml of dichloromethane. The organic phases are dried on MgSO₄, filtered and evaporated, and 2.74 g (11.95 mmol) of tert-butyl 4-(2-aminoethyl)piperidine-1-carboxylate are obtained in the form of a clear oil after purification by flash chromatography on silica gel (eluent: dichloromethane/methanol/NH₄OH=90/9/1percent) Yield: 78percent ¹H NMR (CDCl₃) δ: 1.10 (m, 2H); 1.40 (m, 2H); 1.45 (s, 9H); 1.49 (Is; 3H); 1.64 (m, 2H); 3.58 (m, 4H); 4.07 (m, 2H).
24.7 g	With hydrazine hydrate In ethanol at 50 - 60℃; for 22 h;	To the tert-butyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethyl)piperidine-1-carboxylate (245 g) in ethanol ( 2 L) was added hydrazine hydrate (55 mL, ~1 mol) in one portion and the mixture heated to 50-60 °C for 22 hours. The resulting slurry was cooled to 30 °C, filtered and washed with ethanol (800 mL). The filtrate was evaporated, taken up in CH₂Cl₂ (1.3 L) and re-filtered through a pad of Celite, washing with CH₂Cl₂ (700 mL). This filtrate was washed with 1M sodium hydroxide (1 L), dried (MgSO₄) and evaporated to afford the tert-butyl 4-(2-aminoethyl)piperidine-1-carboxylate (137.8 g) as a hazy yellow oil. The sodium hydroxide layer from above was passed through the solids along with additional CH₂Cl₂ (400 mL). The layers were separated and the organics dried (MgSO₄) and evaporated to afford the amine (24.7 g) as a hazy colorless oil. To the tert-butyl 4-(2-aminoethyl)piperidine-1-carboxylate (228.6 g, 1.0 mol) in CH₂Cl₂ (2 L) at 4 °C was added pyridine (310 mL, 3.8 mol) followed by 2-nitrobenzenesulfonyl chloride (278 g, 1.25 mol) in portions. The mixture was stirred at room temperature overnight then quenched by addition of 2M NaH₂PO₄ (1.4 L). The layers were separated and the aqueous (pH ~5) re-extracted with CH₂Cl₂ (500 mL) then EtOAc (500 mL). The combined organics were dried (MgSO₄) and filtered through a pad of silica (220 g), washing with 20percent EtOAc in CH₂Cl₂ (650 mL). The filtrate was evaporated and azeotroped with toluene to afford crude sulfonamide (400 g). Chromatography (1 kg silica, eluent 2-10percent EtOAc inn CH₂Cl₂) afforded sulfonamide (293.3 g) as a yellow solid. ¹H NMR (500 MHz, CDCl₃) d 8.14 (m, 1H), 7.87 (m, 1H), 7.78-7.74 (m, 2H), 5.22 (t, J = 5.9 Hz, 1H), 4.06 (br s, 2H), 3.14 (m, 2H), 2.16 (br s, 2H), 1.61-1.39 (m, 5H), 1.44 (s, 9H), 1.06 (m, 2H).

Reference： [1] Patent: US2015/336943, 2015, A1, . Location in patent: Paragraph 1414-1416
[2] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 21, p. 4805 - 4811

3
[ 146093-45-0 ]
[ 146093-46-1 ]

Reference： [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 12, p. 1779 - 1788
[2] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 13, p. 2167 - 2172

4
[ 89151-44-0 ]
[ 146093-46-1 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 13, p. 2167 - 2172
[2] Journal of Medicinal Chemistry, 1997, vol. 40, # 12, p. 1779 - 1788
[3] Patent: US2015/336943, 2015, A1,

5
[ 79099-07-3 ]
[ 146093-46-1 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 13, p. 2167 - 2172
[2] Patent: WO2015/138895, 2015, A1,
[3] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 21, p. 4805 - 4811

6
[ 622-26-4 ]
[ 146093-46-1 ]

Reference： [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 12, p. 1779 - 1788

7
[ 24424-99-5 ]
[ 146093-46-1 ]

Reference： [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 12, p. 1779 - 1788

8
[ 89151-46-2 ]
[ 146093-46-1 ]

Reference： [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 12, p. 1779 - 1788

9
[ 147699-19-2 ]
[ 146093-46-1 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 13, p. 2167 - 2172
[2] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 21, p. 4805 - 4811

10
[ 135716-08-4 ]
[ 146093-46-1 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 13, p. 2167 - 2172

11
[ 135716-09-5 ]
[ 146093-46-1 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 13, p. 2167 - 2172

12
[ 146093-46-1 ]
[ 896103-62-1 ]

Reference： [1] Patent: US2014/171403, 2014, A1, . Location in patent: Page/Page column

[ 146093-46-1 ] Synthesis Path-Downstream 1~88

1
(R)-1-{(2S,4R)-4-tert-Butoxy-1-[3,3,3-tris-(4-chloro-phenyl)-propionyl]-pyrrolidine-2-carbonyl}-pyrrolidine-2-carboxylic acid [ No CAS ]
[ 146093-46-1 ]
4-{2-[(1-{4-tert-butoxy-1-[3,3,3-tris-(4-chloro-phenyl)-propionyl]-pyrrolidine-2-carbonyl}-pyrrolidine-2-carbonyl)-amino]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 5653 - 5663

2
[ 1054637-74-9 ]
[ 146093-46-1 ]
4-{2-[(1-{4-tert-butoxy-1-[3,3,3-tris-(4-fluoro-phenyl)-propionyl]-pyrrolidine-2-carbonyl}-pyrrolidine-2-carbonyl)-amino]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 5653 - 5663

3
[ 146093-46-1 ]
[ 323183-79-5 ]
4-[2-({1-[4-tert-butoxy-1-(3,3,3-triphenyl-propionyl)-pyrrolidine-2-carbonyl]-pyrrolidine-2-carbonyl}-amino)-ethyl]-piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 5653 - 5663

4
[ 1722-12-9 ]
[ 146093-46-1 ]
[ 925914-89-2 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 807 - 819

5
[ 959432-07-6 ]
[ 146093-46-1 ]
5-bromo-3-[2-(2-methoxy-ethyl)-6-(2-piperidin-4-yl-ethylamino)-2H-pyrazolo[3,4-d]pyrimidin-4-yl]-1,3-dihydro-indol-2-one hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%		EXAMPLE 227; 5-Bromo-3-[2-(2-methoxy-ethyl)-6-(2-piperidin-4-yl-ethylamino)-2H-pyrazolo[3,4-d]pyrimidin-4-yl]-1,3-dihydro-indol-2-one; Example 225 was reacted with 4-aminoethyl-1-N-BOC piperidine to afford after removal of the BOC group a yellow solid-the hydrochloride salt. Yield: 74%. Example 227: mp 248-51 C.; MS (ES+calculated: 514.43; found: 515.92 M+H). HPLC (97% purity, retention time 7.507 minutes-Method B); 1H NMR (400 MHz, DMSO-d6): delta 11.53 (br s, 1H), 10.08 (br s, 1H), 9.37 (br s, 1H), 8.70 (br s, 1H), 8.39 (br s, 1H), 7.20 (br s, 1H), 7.07 (br s, 1H), 6.70 (br s, 1H), 4.34 (m, 2H), 3.73 (s, 3H), 3.50 (m, 2H), 2.81 (m, 2H), 1.87 (m, 2H), 1.70 (m, 1H), 1.60 (m, 2H), 1.34 (m, 2H).

Reference： [1]Patent: US2007/281949,2007,A1 .Location in patent: Page/Page column 72-73

6
[ 2448-45-5 ]
[ 146093-46-1 ]
C₂₉H₃₉N₃O₅ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4793 - 4807

7
[ 1000771-68-5 ]
[ 146093-46-1 ]
4-[2-(5-chloro-2-{1-[2-(3-oxo-2,3-dihydro-benzo[1,4]oxazin-4-yl)-ethyl]-piperidin-4-yl}-benzoylamino)-ethyl]-piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 6489 - 6492

8
[ 146093-46-1 ]
(2-piperidin-4-yl-ethyl)-pyrimidin-2-yl-amine; hydrochloride [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 807 - 819

9
[ 146093-46-1 ]
4-methylbenzyl 4-[2-(pyrimidin-2-ylamino)ethyl]piperidine-1-carboxylate hydrochloride [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 807 - 819

10
[ 146093-46-1 ]
(R)-1-[(2S,4R)-4-Hydroxy-1-(3,3,3-triphenyl-propionyl)-pyrrolidine-2-carbonyl]-pyrrolidine-2-carboxylic acid (2-piperidin-4-yl-ethyl)-amide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 5653 - 5663

11
[ 146093-46-1 ]
(R)-1-{(2S,4R)-4-Hydroxy-1-[3,3,3-tris-(4-chloro-phenyl)-propionyl]-pyrrolidine-2-carbonyl}-pyrrolidine-2-carboxylic acid (2-piperidin-4-yl-ethyl)-amide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 5653 - 5663

12
[ 146093-46-1 ]
(R)-1-{(2S,4R)-4-Hydroxy-1-[3,3,3-tris-(4-fluoro-phenyl)-propionyl]-pyrrolidine-2-carbonyl}-pyrrolidine-2-carboxylic acid (2-piperidin-4-yl-ethyl)-amide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 5653 - 5663

13
[ 79099-07-3 ]
[ 146093-46-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2167 - 2172
[2]Patent: WO2015/138895,2015,A1
[3]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 4805 - 4811
[4]Patent: WO2019/46778,2019,A1

14
[ 89151-44-0 ]
[ 146093-46-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2167 - 2172
[2]Journal of Medicinal Chemistry,1997,vol. 40,p. 1779 - 1788
[3]Patent: US2015/336943,2015,A1

15
[ 135716-08-4 ]
[ 146093-46-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2167 - 2172

16
[ 146093-46-1 ]
(R)-2-((R)-3,3-Difluoro-cyclopentyl)-2-hydroxy-2-phenyl-N-(2-piperidin-4-yl-ethyl)-acetamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2167 - 2172

17
[ 147699-19-2 ]
[ 146093-46-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2167 - 2172
[2]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 4805 - 4811

18
[ 146093-46-1 ]
[ 162748-86-9 ]