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[ CAS No. 20691-89-8 ] {[proInfo.proName]}

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Chemical Structure| 20691-89-8
Chemical Structure| 20691-89-8
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Product Details of [ 20691-89-8 ]

CAS No. :20691-89-8 MDL No. :MFCD03411903
Formula : C7H15NO Boiling Point : -
Linear Structure Formula :- InChI Key :KJZLJGZZDNGGCA-UHFFFAOYSA-N
M.W : 129.20 Pubchem ID :271971
Synonyms :

Calculated chemistry of [ 20691-89-8 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 41.62
TPSA : 23.47 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.86 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.8
Log Po/w (XLOGP3) : 0.32
Log Po/w (WLOGP) : -0.06
Log Po/w (MLOGP) : 0.57
Log Po/w (SILICOS-IT) : 0.78
Consensus Log Po/w : 0.68

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.78
Solubility : 21.6 mg/ml ; 0.167 mol/l
Class : Very soluble
Log S (Ali) : -0.38
Solubility : 54.3 mg/ml ; 0.421 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.55
Solubility : 36.2 mg/ml ; 0.28 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 20691-89-8 ]

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

Application In Synthesis of [ 20691-89-8 ]

* 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 [ 20691-89-8 ]
  • Downstream synthetic route of [ 20691-89-8 ]

[ 20691-89-8 ] Synthesis Path-Upstream   1~10

  • 1
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YieldReaction ConditionsOperation in experiment
84%
Stage #1: With lithium aluminium tetrahydride In diethyl ether at 0 - 20℃;
Stage #2: With water In diethyl ether for 0.5 h;
Example 23
(1-Methylpiperidin-4-yl)methanol (22):
A solution of ester 21 (10.1 g, 59.0 mmol) in Et2O (40 mL) was added dropwise to a suspension of LiAlH4 (2.46 g, 64.9 mmol) in Et2O (200 mL) at 0° C.
Then, the reaction mixture was allowed to warm to room temperature and was then stirred for 4 h at this temperature.
Water (10 mL) was added slowly and stirring was continued for a further 30 min.
The formed white precipitate was separated by filtration and washed thoroughly with Et2O (250 mL).
After removal of the solvent under reduced pressure the resulting oil was purified by distillation (bp. 108° C., 14 mbar) to give alcohol 22 (6.40 g, 84percent) as a colorless oil. -Rf=0.53 (CH2Cl2/MeOH, 5:1, 5percent NEt3, PMA: dark blue).
1H NMR (300 MHz, CDCl3): δ=1.28 (dq, J=12.2, 3.7 Hz, 2H, 3-Hax, 5-Hax), 1.38-1.55 (m, 1H, 4-H), 1.68-1.79 (m, 2H, 3-Heq, 5-Heq), 1.93 (dt, J=11.8, 2.3 Hz, 2H, 2-Hax, 6-Hax), 2.26 (s, 3H, NMe), 2.82-2.92 (m, 2H, 2-Heq, 6-Heq), 3.12 (sbr, 1H, OH), 3.46 (d, J=6.4 Hz, 2H, CH2OH) ppm. -13C NMR (75.5 MHz, CDCl3): δ=28.8 (C-3, C-5), 37.9 (C-4), 46.3 (NMe), 55.5 (C-2, C-6), 67.4 (CH2OH) ppm. -MS (70 eV, EI): m/z (percent)=129 (55) [M]+, 128 (100) [M-H]+, 112 (10) [M-OH]+, 98 (21) [M-CH2OH]+. -C7H15NO (129.20).
Reference: [1] European Journal of Organic Chemistry, 2006, # 10, p. 2314 - 2321
[2] Patent: US2009/318668, 2009, A1, . Location in patent: Page/Page column 52
[3] Patent: WO2007/89149, 2007, A2, . Location in patent: Page/Page column 96
[4] Journal of the American Chemical Society, 1952, vol. 74, p. 3831
[5] Patent: WO2005/95387, 2005, A1, . Location in patent: Page/Page column 68
  • 2
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  • [ 20691-89-8 ]
YieldReaction ConditionsOperation in experiment
88%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; Inert atmosphere
Stage #2: With water; sodium hydroxide In tetrahydrofuran at 0 - 20℃;
A solution of tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate (1.94 g, 9.0 mmol) in THF (15.0 mL) was added drop-wise to a 1M solution of LiAlH4 in THF (13.5 mL, 13.5 mmol) under argon.
The reaction mixture was stirred at room temperature for 17 hours and then cooled to 0° C. A mixture of THF and water (1:1 ratio, 1.5 mL) was added drop-wise.
A gelatinous white solid formed. 4M aq NaOH solution (0.6 mL) was added drop-wise.
Water (2 mL) was added and the resulting mixture stirred at room temperature for 2 hours.
The white solid was removed by filtration.
The filtrate was loaded onto an Isolute HM-N liquid-liquid extraction column and then eluted with EtOAc (200 mL).
The resulting organic phase concentrated in vacuo yielding (1-methylpiperidin-4-yl)methanol as a yellow oil (1.02 g, 88percent).
Analytical LCMS: purity ~90percent (System B, RT=1.88 min), ES+: 129.8 [MH]+.
(
88%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 17 h; Inert atmosphere
Stage #2: With sodium hydroxide In tetrahydrofuran; water at 0 - 20℃;
A solution of tert-bvXy\\ 4-(hydroxymethyl)piperidine-l-carboxylate (1.94 g, 9.0 mmol) in THF (15 mL) was added drop-wise to IM solution Of LiAlH4 in THF (13.5 mL, 13.5 mmol) under argon. The reaction mixture was stirred at room temperature for 17 hours, cooled to 0 0C and quenched by the dropwise addition of a mixture of THF and water (1 :1 ratio, 1.5 mL). 4M aq NaOH solution (0.6 mL), and water (2.0 mL) were added and the mixture stirred at room temperature for 2 hours. A white solid was removed by filtration. The filtrate was purified by using an Isolute HM-N cartridge, eluting with EtOAc (200 mL). The eluent was concentrated in vacuo yielding (l-methylpiperidin-4-yl)methanol (1.02 g, 88percent) as a yellow oil. Analytical LCMS: (System A, Rτ = 0.32 min), ES+: 130.3 [MH]+.
Reference: [1] Patent: US2009/281087, 2009, A1, . Location in patent: Page/Page column 9-10
[2] Patent: WO2009/147219, 2009, A1, . Location in patent: Page/Page column 23
[3] Patent: WO2009/71677, 2009, A1, . Location in patent: Page/Page column 22
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Reference: [1] Patent: US2003/125339, 2003, A1,
[2] Patent: US6878714, 2005, B2,
[3] Patent: WO2009/147219, 2009, A1,
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  • [ 36166-75-3 ]
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Reference: [1] Patent: US5945434, 1999, A,
  • 5
  • [ 100-58-3 ]
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Reference: [1] Patent: US6486354, 2002, B1,
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Reference: [1] Patent: US2003/225106, 2003, A1, . Location in patent: Page 52-53; 72; 73; 128
  • 7
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Reference: [1] European Journal of Organic Chemistry, 2006, # 10, p. 2314 - 2321
  • 8
  • [ 1570-45-2 ]
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Reference: [1] Journal of the American Chemical Society, 1952, vol. 74, p. 3831
  • 9
  • [ 1690-75-1 ]
  • [ 20691-89-8 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1959, vol. 24, p. 212,216
  • 10
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  • [ 68947-43-3 ]
  • [ 20845-32-3 ]
Reference: [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 25, p. 7212 - 7217[2] Angew. Chem., 2016, vol. 128, # 25, p. 7328 - 7333,6
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