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[ CAS No. 171049-35-7 ] {[proInfo.proName]}

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Chemical Structure| 171049-35-7
Chemical Structure| 171049-35-7
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Product Details of [ 171049-35-7 ]

CAS No. :171049-35-7 MDL No. :MFCD02179169
Formula : C15H28N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :NERBLCVCQKXTEP-UHFFFAOYSA-N
M.W : 268.40 Pubchem ID :11747599
Synonyms :

Calculated chemistry of [ 171049-35-7 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.93
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 85.23
TPSA : 41.57 Ų

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) : -6.4 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.38
Log Po/w (XLOGP3) : 2.17
Log Po/w (WLOGP) : 1.87
Log Po/w (MLOGP) : 2.23
Log Po/w (SILICOS-IT) : 1.93
Consensus Log Po/w : 2.32

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.61
Solubility : 0.663 mg/ml ; 0.00247 mol/l
Class : Soluble
Log S (Ali) : -2.68
Solubility : 0.566 mg/ml ; 0.00211 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.48
Solubility : 0.881 mg/ml ; 0.00328 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.47

Safety of [ 171049-35-7 ]

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 [ 171049-35-7 ]

* 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 [ 171049-35-7 ]
  • Downstream synthetic route of [ 171049-35-7 ]

[ 171049-35-7 ] Synthesis Path-Upstream   1~6

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YieldReaction ConditionsOperation in experiment
72% With sodium hydroxide In ethanol; water at 0 - 10℃; for 1 h; PREPARATION LXXXIX; 4-(4-piperidinyl)-1-piperidinecarboxylic acid, 1,1-dimethylethyl ester; A solution is prepared of 41 g (0.17 M) of 4,4'-bipiperidine dihydrochloride in 250 ml of ethanol and 250 ml of 2N sodium hydroxide. A solution of 18.5 g (0.085 M) of t-butyl dicarbonate in 100 ml of ethanol are added slowly, at 0° C. The reaction mixture is agitated for 1 hour at 10° C. and the ethanol is then removed by an evaporator, under reduced pressure. The residual aqueous phase is saturated with sodium chloride and extracted with ethyl acetate. The organic phase obtained is dried over magnesium sulphate and concentrated under reduced pressure. The crude product is purified by silica gel chromatography in eluting with the aid of a dichloromehane/methanol/aqueous ammonia mixture (8/2/0.4; v/v/v). 16.5 g of the compound sought after are thus obtained as a white solid (yield=72percent). M.Pt.=70-71° C.
63% With sodium hydroxide In ethanol; water PREPARATION 9
Preparation of N-(t-butoxycarbonyl)-4,4'-bipiperidine
4,4'-Bipiperidine dihydrochloride (2.5 g, 10 mmol) was dissolved in water (10 mL) and treated with 5N sodium hydroxide to pH 8-9, diluted to 120 mL with ethanol and stirred at RT.
The resulting mixture was treated with di-t-butyl dicarbonate (2.4 g, 11 mmol) in ethanol (80 mL) in one portion and the mixture stirred at RT, with periodic additions of 5N sodium hydroxide to maintain a pH of 8-9.
After 5 h. the mixture was concentrated and the residue was dissolved in a mixture of 1:1 ether:water (100 mL) and the pH adjusted to 12 with 5N sodium hydroxide.
The aqueous phase was extracted with ether and the organic phase was washed sequentially with brine, dilute citric acid, and water.
The aqueous phase was adjusted to pH 12-13 with 5N sodium hydroxide and extracted with ether.
The organic phase was washed with brine, dried (sodium sulfate), concentrated to a clear oil and dried in vacuo to give the title compound (1.7 g, 63percent) as a solid. TLC Rf 0.4 (Kieselgel 60 F254, 15:3:2 2-butanol:formic acid:water); MS (ES) m/e 268.3 [M+H]+.
Reference: [1] Patent: US2006/178360, 2006, A1, . Location in patent: Page/Page column 17
[2] Patent: US6008213, 1999, A,
[3] Journal of Medicinal Chemistry, 2016, vol. 59, # 7, p. 3489 - 3498
[4] Patent: WO2017/83219, 2017, A1, . Location in patent: Page/Page column 43; 44
  • 2
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YieldReaction ConditionsOperation in experiment
45% for 8 h; To 4,4'-bipiperidine (5.48 g, 32.6 mmol) in THF (160 mL) and CHCl3 (160 mL) was added BOC-On (4.01 g) in THF (90 mL) dropwise over a 8 h period. The reaction was then concentrated and purified by flash chromatography. The residue was taken up in 1M KHSO4 (250 mL) and washed with diethyl ether (three times). K2CO3 (38.0 g, 275 mmol) was added to the aqueous layer which was subsequently extracted with CHCl3 (3.x.), dried (MgSO4) and concentrated to provide the title compound of step A (1.98 g, 7.40 mmol, 45percent). 1H NMR (400 MHz, CDCl3) δ ppm 1.06-1.18 (m, 5H), 1.42 (s, 9H), 1.58-1.69 (m, 6H), 2.50-2.61 (m, 4H), 3.06 (d, J=12.1 Hz, 2H), 4.08 (br. s., 2H).
45%
Stage #1: for 8 h;
Stage #2: With potassium hydrogensulfate In water
Stage #3: With potassium carbonate In water
Intermediate B114: 2-(methyloxy)-4-{1'-[2-(methylsulfonyl)ethyl]-4,4'- bipiperidin-1-yl}aniline; Step A/Intermediate B1 15: 1 ,1-dimethylethyl 4,4'-bipiperidine-1-carboxylate; To 4,4'-bipiperidine (5.48 g, 32.6 mmol) in tetrahydrofuran (160 ml.) and chloroform (160 ml.) was added BOC-ON (4.01 g, 16.2 mmol) in tetrahydrofuran (90 ml.) dropwise over an 8 hour period. The reaction was then concentrated and purified by chromatograpy on Siψ2. The residue was taken up in 1 M KHSO4 (250 ml.) and washed with diethyl ether (three times). Potassium carbonate (38.0 g, 275 mmol) was added to the aqueous layer which was subsequently extracted with chloroform (three times), dried (MgSO4), and concentrated to provide 1 ,1-dimethylethyl 4,4'- bipiperidine-1-carboxylate (1.98 g, 7.40 mmol, 45percent). 1 H NMR (400 MHz, CDCI3) δ ppm 1.06 - 1.18 (m, 6 H), 1.42 (s, 9 H), 1.58 - 1.69 (m, 6 H), 2.50 - 2.61 (m, 4 H), 3.06 (d, J=12.1 Hz, 2 H), 4.08 (br s, 1 H).
Reference: [1] Journal of Medicinal Chemistry, 2001, vol. 44, # 24, p. 4035 - 4038
[2] Journal of Medicinal Chemistry, 2005, vol. 48, # 20, p. 6491 - 6503
[3] Patent: US2008/300242, 2008, A1, . Location in patent: Page/Page column 105
[4] Patent: WO2009/20990, 2009, A1, . Location in patent: Page/Page column 144
  • 3
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YieldReaction ConditionsOperation in experiment
63% With sodium hydroxide In ethanol; water Preparation 22
Preparation of N-(t-butoxycarbonyl)-4,4'-bipiperdine
4,4'-Bipiperidine dihydrochloride (2.5 g, 10 mmol) was dissolved in water (10 mL) and treated with 5N sodium hydroxide to pH 8-9, diluted to 120 mL with ethanol and stirred at RT.
The resulting mixture was treated with di-t-butyl dicarbonate (2.4 g, 11 mmol) in ethanol (80 mL) in one portion and the mixture stirred at RT, with periodic additions of 5N sodium hydroxide to maintain a pH of 8-9.
After 5 h, the mixture was concentrated and the residue was dissolved in a mixture of 1:1 ether water (100 mL) and the pH adjusted to 12 with 5N sodium hydroxide.
The aqueous phase was extracted with ether and the organic phase was washed sequentially with brine, dilute citric acid, and water.
The aqueous phase was adjusted to pH 12-13 with 5N sodium hydroxide and extracted with ether.
The organic phase was washed with brine, dried (sodium sulfate), concentrated to a clear oil and dried in vacuo to give the title compound (1.7 g, 63percent) as a solid. TLC Rf 0.4 (Kieselgel 60 F254, 15:3:2 2-butanol:formic acid:water); MS (ES) m/e 268.3 [M+H]+.
Reference: [1] Patent: US6403578, 2002, B1,
  • 4
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Reference: [1] Patent: US2004/138226, 2004, A1, . Location in patent: Page 21
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Reference: [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 20, p. 6491 - 6503
  • 6
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 8, p. 2224 - 2229
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