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CAS No. :22090-24-0 MDL No. :MFCD00587602
Formula : C12H15NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :DGJNUESQBVPXAY-UHFFFAOYSA-N
M.W : 205.25 Pubchem ID :764599
Synonyms :

Safety of [ 22090-24-0 ]

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 [ 22090-24-0 ]

* 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 [ 22090-24-0 ]
  • Downstream synthetic route of [ 22090-24-0 ]

[ 22090-24-0 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 1204-85-9 ]
  • [ 22090-24-0 ]
YieldReaction ConditionsOperation in experiment
88% at 100℃; for 18 h; Example 113 10-(4-PIPERIDIN-1-YLBENZOYL)-N-(PYRIDIN-3-YLMETHYL)-10,11-DIHYDRO-5H-PYRROLO[2,1-C][1,4]BENZODIAZEPINE-3-CARBOXAMIDE Step A. 4-Piperidin-1-ylbenzonitrile; A mixture of 4-fluorobenzonitrile (1 g, 8.26 mmol), piperidine (0.90 mL, 9.08 mmol) and potassium carbonate (2.28 g, 16.51 mmol) in dry 1-methyl-2-pyrrolidinone (10 mL) was stirred at 120° C. under nitrogen for 20 hours. The cooled reaction mixture was then diluted with water (100 mL) and extracted with ethyl acetate (100 mL). The organic extract was washed with water (100 mL) and brine (100 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo to afford an orange oil. Purification by flash chromatography using a solvent gradient of 1 to 7percent ethyl acetate in hexane gave an orange oil that was crystallized from hexane to afford the title compound (1.41 g, 92percent) as an orange crystalline solid, m.p. 54° C. MS [(+)ESI, m/z]: 187 [M+H]+ Anal. Calcd for C12H14N2: C, 77.38; H, 7.58; N, 15.04. Found: C, 77.30; H, 7.41; N, 15.06.
Reference: [1] Patent: US2006/287522, 2006, A1, . Location in patent: Page/Page column 54
[2] Journal of the American Chemical Society, 1940, vol. 62, p. 2995,3001
[3] Molecular Crystals and Liquid Crystals (1969-1991), 1985, vol. 124, p. 269 - 276
  • 2
  • [ 101038-65-7 ]
  • [ 22090-24-0 ]
YieldReaction ConditionsOperation in experiment
51.3%
Stage #1: With sodium hydroxide; water In ethanol at 60℃; for 2 h;
Stage #2: With hydrogenchloride In ethanol; water
2.7.b
4-piperidin-1-yl-benzoic acid
0.78 mL (0.74 mmol) of 2N NaOH are added to a solution of 350 mg (1.50 mmol) of ethyl 4-piperidin-1-yl-benzoate in 10 mL ethanol.
The reaction solution is stirred for 2 h at 60° C. and then the pH is adjusted to 6-7 with 1N HCl.
The precipitate formed is dried overnight after filtration under high vacuum.
Yield: 158 mg (51.3percent of theory);
C12H15NO2 (M=205.259);
calc.: molar peak (M+H)+: 206 fnd.: molar peak (M+H)+: 206;
Retention time HPLC: 6.2 min (method A).
Reference: [1] Patent: US2004/242572, 2004, A1, . Location in patent: Page/Page column 59
[2] Patent: WO2015/158908, 2015, A1, . Location in patent: Page/Page column 90
  • 3
  • [ 10338-57-5 ]
  • [ 22090-24-0 ]
YieldReaction ConditionsOperation in experiment
67% With potassium hydroxide; sodium hydroxide In neat (no solvent)Heating General procedure: Potassium hydroxide (3.6 g, 64 mmol) and sodium hydroxide (2.4 g, 60 mmol) weremixed and quickly crushed in a porcelain dish. Then the corresponding aldehyde(15 mmol) was added and the mixture was heated on a hot-plate under stirring until thealdehyde melted and additionally 5 minutes. When liquid aldehydes were used, heatingwas continued until temperature reached 140C. After cooling, the crude solid productmixture was added to water (100 mL) and ice (30 g) and acidified with hydrochloric acidto pH 4. The precipitate was collected, dried and recrystallized from ethanol.
Reference: [1] Organic Preparations and Procedures International, 2017, vol. 49, # 1, p. 45 - 52
  • 4
  • [ 10338-58-6 ]
  • [ 22090-24-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 9, p. 3703 - 3726
[2] Patent: WO2009/43890, 2009, A1, . Location in patent: Page/Page column 55-56
  • 5
  • [ 110-89-4 ]
  • [ 456-22-4 ]
  • [ 22090-24-0 ]
Reference: [1] Journal of Organic Chemistry, 1987, vol. 52, # 9, p. 1710 - 1713
  • 6
  • [ 110-89-4 ]
  • [ 22090-24-0 ]
Reference: [1] Journal of the American Chemical Society, 1940, vol. 62, p. 2995,3001
[2] Patent: WO2015/158908, 2015, A1,
[3] Journal of Medicinal Chemistry, 2017, vol. 60, # 9, p. 3703 - 3726
  • 7
  • [ 623-00-7 ]
  • [ 22090-24-0 ]
Reference: [1] Journal of the American Chemical Society, 1940, vol. 62, p. 2995,3001
  • 8
  • [ 1194-02-1 ]
  • [ 22090-24-0 ]
Reference: [1] Molecular Crystals and Liquid Crystals (1969-1991), 1985, vol. 124, p. 269 - 276
  • 9
  • [ 10342-85-5 ]
  • [ 22090-24-0 ]
Reference: [1] Letters in Organic Chemistry, 2014, vol. 11, # 9, p. 651 - 656
  • 10
  • [ 451-46-7 ]
  • [ 22090-24-0 ]
Reference: [1] Patent: WO2015/158908, 2015, A1,
  • 11
  • [ 403-33-8 ]
  • [ 22090-24-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 9, p. 3703 - 3726
  • 12
  • [ 10342-85-5 ]
  • [ 22090-24-0 ]
Reference: [1] Letters in Organic Chemistry, 2014, vol. 11, # 9, p. 651 - 656
  • 13
  • [ 1171309-72-0 ]
  • [ 22090-24-0 ]
Reference: [1] Letters in Organic Chemistry, 2014, vol. 11, # 9, p. 651 - 656
  • 14
  • [ 1171309-72-0 ]
  • [ 22090-24-0 ]
Reference: [1] Letters in Organic Chemistry, 2014, vol. 11, # 9, p. 651 - 656
  • 15
  • [ 111-24-0 ]
  • [ 150-13-0 ]
  • [ 22090-24-0 ]
Reference: [1] Chemische Berichte, 1907, vol. 40, p. 857
[2] Chemische Berichte, 1907, vol. 40, p. 857
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