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[ CAS No. 156185-63-6 ] {[proInfo.proName]}

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Chemical Structure| 156185-63-6
Chemical Structure| 156185-63-6
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Product Details of [ 156185-63-6 ]

CAS No. :156185-63-6 MDL No. :MFCD02677712
Formula : C13H25NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :OXPWHPCCUXESFQ-UHFFFAOYSA-N
M.W : 243.34 Pubchem ID :2800739
Synonyms :

Calculated chemistry of [ 156185-63-6 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.92
Num. rotatable bonds : 6
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 72.18
TPSA : 49.77 Ų

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) : -6.44 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.11
Log Po/w (XLOGP3) : 1.89
Log Po/w (WLOGP) : 2.03
Log Po/w (MLOGP) : 1.71
Log Po/w (SILICOS-IT) : 1.71
Consensus Log Po/w : 2.09

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.14
Solubility : 1.75 mg/ml ; 0.00719 mol/l
Class : Soluble
Log S (Ali) : -2.56
Solubility : 0.674 mg/ml ; 0.00277 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.92
Solubility : 2.93 mg/ml ; 0.0121 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.3

Safety of [ 156185-63-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 156185-63-6 ]

* 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 [ 156185-63-6 ]
  • Downstream synthetic route of [ 156185-63-6 ]

[ 156185-63-6 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 156185-63-6 ]
  • [ 7037-49-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 15, p. 5123 - 5128
[2] Patent: WO2018/68297, 2018, A1, . Location in patent: Page/Page column 39
  • 2
  • [ 7037-49-2 ]
  • [ 24424-99-5 ]
  • [ 156185-63-6 ]
YieldReaction ConditionsOperation in experiment
88% at 20℃; for 2 h; Preparation 144-(3-Aminopropyl)-piperidine-1-carboxylic acid tert-butyl ester(A). Preparation of 4-(3-hydroxypropyl)-piperidine-1-carboxylic acid tert-butyl ester; Di-tert-butyl dicarbonate (3.66 g, 16.8 mmol) is added to a stirred solution of 3-piperidin-4-yl-propan-1-ol (1.60 g, 11.2 mmol) in anhydrous dichloromethane (20 mL) at ambient temperature under nitrogen. The resultant mixture is allowed to stir for 2 hours. The mixture is directly subjected to chromatography purification on silica gel and eluted with MeOH in dichloromethane 0-3percent to give the title compound as a clear oil (2.40 g, 88percent yield).
Reference: [1] Organic Letters, 2002, vol. 4, # 4, p. 549 - 552
[2] Patent: US2008/306082, 2008, A1, . Location in patent: Page/Page column 5-6
[3] Patent: US6235731, 2001, B1,
[4] Organic and Biomolecular Chemistry, 2014, vol. 12, # 5, p. 783 - 794
[5] Tetrahedron, 1999, vol. 55, # 39, p. 11619 - 11639
[6] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 15, p. 2031 - 2034
[7] Patent: WO2018/68297, 2018, A1, . Location in patent: Page/Page column 55
  • 3
  • [ 24424-99-5 ]
  • [ 156185-63-6 ]
YieldReaction ConditionsOperation in experiment
82% With sodium hydroxide In 1,4-dioxane; water for 2 h; 3- (N-Boe-Piperidin-4-yl)-propan-1-ol:; crude 3-piperidin-4-yl- propan-l-ol (73 mmol) was dissolved in dioxane (100 mL) and 3N NaOH (25 mL) was added to give a pH9 solution. Di-tert-butyl dicarbonate (16.0 g, 73 mmol) in dioxane (35 mL) was added dropwise, with simultaneous addition of 3N NaOH to maintain the solution at approximately pH9. After 2 hours no residual amine was visible by TLC (ninhydrin stain) and the reaction was diluted with water (200 mL)and extracted with ethyl acetate (3 x 100 mL). The combined extracts were washed with water and brine and dried (MgS04). Removal of solvent afforded 20 g crude product which was purified by silica gel chromatography (200 g silica) in a sintered glass funnel (L. M. Harwood, Aldrichimica Acta, 1985, 18, 25) eluted with 500 mL each of hexane, 20percent, 40percent, 60percent and 80percent ethyl acetate in hexane. 3-(N-Boc-Piperidin-4-yl)- propan-1-ol was isolated as a clear, colorless oil (14.5 g, 82percent). 1H NMR (500 MHz, CDC13) D 4.09 (2H, m), 3.66 (2H, t), 2.69 (2H, dt), 1.7-1.5 (4H, m), 1.47 (9H, s), 1.4 - 1.3 (5H, m), 1.12 (2H, m).
82% With sodium hydroxide In 1,4-dioxane; water for 2 h; 3-(N-BOC-PIPERIDIN-4-YL)-PROPAN-1-OL : The crude 3-PIPERIDIN-4-YL-PROPAN-1-OL (73 mmol) was dissolved in dioxane (100 mL) and 3N NaOH (25 ML) was added to give a pH9 solution. Di-tert-butyl dicarbonate (16.0 g, 73 mmol) in dioxane (35 ML) was added dropwise, with simultaneous addition of 3N NaOH to maintain the solution at approximately pH9. After 2 hours no residual amine was visible by TLC (ninhydrin stain) and the reaction was diluted with water (200 ML) and extracted with ethyl acetate (3 x 100 mL). The combined extracts were washed with water and brine and dried (MGS04). Removal of solvent afforded 20 g crude product which was purified by silica gel chromatography (200 g silica) in a sintered glass funnel (L. M. Harwood, Aldrichimica Acta, 1985,18, 25) eluted with 500 mL each of hexane, 20percent, 40percent, 60percent and 80percent ethyl acetate in hexane. 3- (N-Boc-Piperidin-4-yl)- PROPAN-1-OL was isolated as a clear, colorless oil (14.5 g, 82percent). LH NMR (500 MHz, CDCl3) 8 4.09 (2H, m), 3.66 (2H, t), 2.69 (2H, dt), 1.7-1. 5 (4H, m), 1.47 (9H, s), 1.4-1. 3 (5H, m), 1.12 (2H, m).
82% With sodium hydroxide In 1,4-dioxane; water for 2 h; Step B: The crude 3-piperidin-4-yl-propan-l-ol (73 mmol) was dissolved in dioxane (100 mL) and 3N NaOH (25 mL) was added to give a pH9 solution. Di-tert-butyl dicarbonate (16.0 g, 73 mmol) in dioxane (35 mL) was added dropwise, with simultaneous addition of 3N NaOH to maintain the solution at approximately pH 9. After 2 hours no residual amine was visible by TLC analysis (ninhydrin stain) and the reaction was diluted with water (200 mL) and extracted with ethyl acetate (3 x 100 mL). The combined extracts were washed with water and brine and dried (MgS04). Removal of solvent afforded 20 g crude product which was purified by silica gel chromatography (200 g silica) in a sintered glass funnel (L. M. Harwood, Aldrichimica Acta, 1985,18, 25) eluted with 500 mL each of hexane, 20percent, 40percent, 60percent and 80percent ethyl acetate in hexane to afford 3-(N-Boc-piperidin-4-yl)-propan-l-ol as a clear, colorless oil (14.5 g, 82percent). 1H NMR (CDC13) 8 4.09 (2H, m), 3.66 (2H, t), 2.69 (2H, dt), 1.7-1.5 (4H, m), 1.47 (9H, s), 1.4 - 1.3 (5H, m), 1.12 (2H, m).
Reference: [1] Patent: WO2005/103050, 2005, A2, . Location in patent: Page/Page column 174
[2] Patent: WO2004/41813, 2004, A1, . Location in patent: Page 118-119
[3] Patent: WO2005/105780, 2005, A2, . Location in patent: Page/Page column 72
  • 4
  • [ 162504-75-8 ]
  • [ 156185-63-6 ]
YieldReaction ConditionsOperation in experiment
4.5 g With diisobutylaluminium hydride In dichloromethane at -78 - 0℃; for 2 h; Inert atmosphere In a 500-ml flask swept with nitrogen, 5 g (17.53 mmol) of tert-butyl 4-(3-methoxy-3-oxopropyl)piperidine-1-carboxylate (prepared according to the method reported in J. Med. Chem.
1995, 38, p 3332-3341 by taking commercial tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate as the starting product) in 100 ml of dichloromethane.
The medium is cooled to -78° C. and 52.6 ml (52.6 mmol) of a 1 M solution of DIBAL-H in dichloromethane are added dropwise.
It is stirred for 2 h at 0° C.
It is cooled to -78° C. and a saturated solution of potassium sodium tartrate is added.
After return to room temperature, it is extracted and then the organic phase is dried on Na2SO4, filtered and evaporated, and 4.5 g of the crude oil are obtained, used as is in the next step.
Reference: [1] Patent: US2015/336943, 2015, A1, . Location in patent: Paragraph 1429-1430
  • 5
  • [ 2629-72-3 ]
  • [ 156185-63-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 15, p. 2031 - 2034
[2] Organic Letters, 2002, vol. 4, # 4, p. 549 - 552
[3] Tetrahedron, 1999, vol. 55, # 39, p. 11619 - 11639
[4] Journal of Medicinal Chemistry, 1994, vol. 37, # 16, p. 2537 - 2551
[5] Patent: WO2018/68297, 2018, A1,
[6] Patent: WO2005/105780, 2005, A2,
  • 6
  • [ 24424-99-5 ]
  • [ 156185-63-6 ]
Reference: [1] Patent: WO2008/97428, 2008, A2, . Location in patent: Page/Page column 92
  • 7
  • [ 104-58-5 ]
  • [ 24424-99-5 ]
  • [ 156185-63-6 ]
Reference: [1] Patent: US6362188, 2002, B1,
  • 8
  • [ 7037-49-2 ]
  • [ 34619-03-9 ]
  • [ 156185-63-6 ]
Reference: [1] Journal of Medicinal Chemistry, 1994, vol. 37, # 16, p. 2537 - 2551
[2] Patent: US5714497, 1998, A,
  • 9
  • [ 403802-41-5 ]
  • [ 156185-63-6 ]
Reference: [1] Patent: US2002/68753, 2002, A1,
  • 10
  • [ 24424-99-5 ]
  • [ 109438-76-8 ]
  • [ 156185-63-6 ]
Reference: [1] Patent: US5563158, 1996, A,
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