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[ CAS No. 26905-02-2 ] {[proInfo.proName]}

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Chemical Structure| 26905-02-2
Chemical Structure| 26905-02-2
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Product Details of [ 26905-02-2 ]

CAS No. :26905-02-2 MDL No. :MFCD03077010
Formula : C11H14ClN Boiling Point : -
Linear Structure Formula :- InChI Key :VKQHTSSNSJIMAL-UHFFFAOYSA-N
M.W : 195.69 Pubchem ID :1203613
Synonyms :

Calculated chemistry of [ 26905-02-2 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.45
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 60.25
TPSA : 12.03 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.35 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.59
Log Po/w (XLOGP3) : 3.02
Log Po/w (WLOGP) : 2.43
Log Po/w (MLOGP) : 2.94
Log Po/w (SILICOS-IT) : 3.37
Consensus Log Po/w : 2.87

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.23
Solubility : 0.115 mg/ml ; 0.000587 mol/l
Class : Soluble
Log S (Ali) : -2.94
Solubility : 0.226 mg/ml ; 0.00115 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.23
Solubility : 0.0116 mg/ml ; 0.0000594 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.19

Safety of [ 26905-02-2 ]

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 [ 26905-02-2 ]

* 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 [ 26905-02-2 ]
  • Downstream synthetic route of [ 26905-02-2 ]

[ 26905-02-2 ] Synthesis Path-Upstream   1~23

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Reference: [1] Organic Letters, 2017, vol. 19, # 3, p. 572 - 575
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YieldReaction ConditionsOperation in experiment
75.3% With hydrogen In methanol at 20℃; for 7 h; 2.19.a
4-(4-chloro-phenyl)-piperidine
To a solution of 5.0 g (21.7 mmol) of 4-(4-chloro-phenyl)-1,2,3,6-tetrahydro-pyridine (cf. 2.13.a) in 20 mL methanol are added 500 mg Pd/C.
The reaction mixture is stirred for 7 h at ambient temperature and 10 psi hydrogen.
After separation of the catalyst the solvent is eliminated using the rotary evaporator.
Further purification is carried out by column chromatography on silica gel (eluant: dichloromethane/methanol/ammonia=5:4.9:0.1).
Yield: 3.2 (75.3percent of theory);
C11H14ClN (M=195.694);
calc.: molar peak (M+H)+: 196/198 fnd.: molar peak (M+H)+: 196/198.
Rf value: 0.37 (silica gel, dichloromethane/methanol/NH3 5:4.9:0.1).
Reference: [1] Patent: US5489599, 1996, A,
[2] Patent: US2004/242572, 2004, A1, . Location in patent: Page/Page column 63-63
[3] Medicinal Chemistry Research, 1999, vol. 9, # 9, p. 686 - 695
[4] Journal of Medicinal Chemistry, 2004, vol. 47, # 3, p. 497 - 508
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YieldReaction ConditionsOperation in experiment
70% With trifluoroacetic acid In dichloromethane at 20℃; Compound 42.4. 4-(4-Chlorophenyl)piperidine. Into a 250-mL round-bottom flask, was placed a solution of ter/-butyl 4-(4-chlorophenyl)piperidine-l -carboxylate (compound 42.3, 5.00 g, 16.9 mmol) in dichloromethane (100 mL), trifluoroacetic acid (9.6 g, 84 mmol). The resulting solution was stirred overnight at room temperature and then concentrated under reduced pressure. The residue was carefully diluted with ethyl acetate (100 mL) and aqueous sodium bicarbonate was added until a pH of 8 was attained. The resulting mixture was washed with brine (100 mL) and the organic layer was dried (Na2S04), filtered, and concentrated under reduced pressure to yield the title compound as a light yellow solid (2.30
70% With trifluoroacetic acid In dichloromethane at 20℃; Compound 42.4. 4-(4-Chlorophenyl)piperidine.
Into a 250-mL round-bottom flask, was placed a solution of tert-butyl 4-(4-chlorophenyl)piperidine-l-carboxylate (compound 42.3, 5.00 g, 16.9 mmol) in dichloromethane (100 mL), trifluoroacetic acid (9.6 g, 84 mmol). The resulting solution was stirred overnight at room temperature and then concentrated under reduced pressure. The residue was carefully diluted with ethyl acetate (100 mL) and aqueous sodium bicarbonate was added until a pH of 8 was attained. The resulting mixture was washed with brine (100 mL) and the organic layer was dried (Na2S04), filtered, and concentrated under reduced pressure to yield the title compound as a light yellow solid (2.30 9, 70percent).
Reference: [1] Patent: WO2014/8197, 2014, A1, . Location in patent: Page/Page column 113
[2] Patent: WO2015/95767, 2015, A1, . Location in patent: Page/Page column 127; 128
[3] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 10, p. 1731 - 1735
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 4, p. 495 - 500
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 24, p. 7381 - 7384
[2] Patent: WO2014/8197, 2014, A1,
[3] Patent: WO2015/95767, 2015, A1,
[4] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 10, p. 1731 - 1735
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Reference: [1] Patent: US2012/35143, 2012, A1,
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Reference: [1] Patent: US2012/35143, 2012, A1,
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Reference: [1] Patent: US2012/35143, 2012, A1,
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 4, p. 495 - 500
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 4, p. 495 - 500
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 4, p. 495 - 500
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 4, p. 495 - 500
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 4, p. 495 - 500
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  • [ 79099-07-3 ]
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Reference: [1] Patent: WO2014/8197, 2014, A1,
[2] Patent: WO2015/95767, 2015, A1,
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  • [ 235109-63-4 ]
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Reference: [1] Patent: WO2014/8197, 2014, A1,
[2] Patent: WO2015/95767, 2015, A1,
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Reference: [1] Patent: WO2014/8197, 2014, A1,
[2] Patent: WO2015/95767, 2015, A1,
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Reference: [1] Patent: US2012/35143, 2012, A1,
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Reference: [1] Patent: US2012/35143, 2012, A1,
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 10, p. 1731 - 1735
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 10, p. 1731 - 1735
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Reference: [1] Tetrahedron Letters, 2001, vol. 42, # 34, p. 5821 - 5823
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Reference: [1] Tetrahedron Letters, 2001, vol. 42, # 34, p. 5821 - 5823
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Reference: [1] Tetrahedron Letters, 2001, vol. 42, # 34, p. 5821 - 5823
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