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[ CAS No. 162046-66-4 ]

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Chemical Structure| 162046-66-4
Chemical Structure| 162046-66-4
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CAS No. :162046-66-4 MDL No. :MFCD04115067
Formula : C16H22N2O4 Boiling Point : 476.9°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :306.36 g/mol Pubchem ID :2795508
Synonyms :

Safety of [ 162046-66-4 ]

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 [ 162046-66-4 ]

  • Upstream synthesis route of [ 162046-66-4 ]
  • Downstream synthetic route of [ 162046-66-4 ]

[ 162046-66-4 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 158985-36-5 ]
  • [ 162046-66-4 ]
YieldReaction ConditionsOperation in experiment
100% With ethanol; sodium hydroxide In tetrahydrofuran at 60℃; for 3 h; A mixture of compound 2 (3.2 g, 10 mmol) and 2M NaOH (50 mE) in THF (50 ml) and EtOH (50 mE) was stirred at 60° C. for 3 hours. The mixture was concentrated to obtain a residue, HC1 (2 M) was added to adjust pH to 7, filtered to give compound 3 as a white solid (3.0 g, 100percent).
83% at 20 - 50℃; for 4 h; A mixture of 16a (4.0 g, 12.5 mmol), in THF (125 mL) and MeOH (31 mL) wasstirred room temperature until a clear solution was obtained, followed by theaddition of 1 N NaOH (125 mL) was added. The mixture was stirred at 50 °C for4 hours after which TLC indicated completed consumption of 16a. The reactionmixture was cooled to room temperature and then poured into an aqueoussolution of HCl (1 M, 200 mL) resulting in the formation of a white precipitate.The mixture was left to stir at room temperature for 30 minutes and theprecipitate was collected via filtration, washed with water (15 mL), and air driedfor 24 hours to give 16b as a white solid (3.17 g, 83percent).1H NMR (400 MHz, DMSO-d6): δ 1.42 (s, 9H), 3.24 – 3.36 (m, 4H), 3.39 – 3.51(m, 4H), 6.96 (d, J = 8.8 Hz, 1H), 7.78 (d, J = 8.8 Hz, 1H). 13C NMR (100 MHz,DMSO-d6): δ 28.65, 47.23, 79.67, 114.22, 120.33, 131.45, 154.11, 154.46,167.81.
Reference: [1] Patent: US2018/141923, 2018, A1, . Location in patent: Paragraph 0257; 0260; 0261; 0284; 0285
[2] Molecular Pharmacology, 2016, vol. 90, # 2, p. 80 - 95
[3] Patent: WO2006/38039, 2006, A1, . Location in patent: Page/Page column 15
[4] Patent: US5648368, 1997, A,
[5] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 6, p. 1779 - 1783
[6] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 15, p. 4646 - 4661
[7] Patent: WO2008/148840, 2008, A1, . Location in patent: Page/Page column 66
  • 2
  • [ 234082-33-8 ]
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YieldReaction ConditionsOperation in experiment
87% With sodium hydroxide In ethanol (b)
4-(4-(tert-butoxycarbonyl)piperazin-1-yl)benzoic acid
To a mixture of 4-(4-ethoxycarbonyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (10 g, 29.9 mmol) in ethanol (200 mL was added 1 N sodium hydroxide (100 mL).
The reaction mixture was stirred at 70° C. overnight.
The solvent was removed under vacuum and the residue washed twice with ethyl acetate, acidified to pH 6 with 5 N HCl, filtered, and concentrated to dryness to provide the title compound (8 g, 87percent yield) as a white solid. 1H NMR (d6-DMSO, 400 MHz) δ (ppm) 7.74 (m, 2H), 6.92 (m, 2H), 3.90 (m, 2H), 3.42 (m, 2H), 3.25 (m, 4H), 1.38 (s, 9H).
Reference: [1] Patent: US2012/114600, 2012, A1,
[2] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 6, p. 629 - 634
[3] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 7, p. 2089 - 2108
[4] Journal of Medicinal Chemistry, 2006, vol. 49, # 3, p. 1165 - 1181
  • 3
  • [ 24424-99-5 ]
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YieldReaction ConditionsOperation in experiment
45% With potassium carbonate In tetrahydrofuran; water at 0 - 20℃; for 4 h; To a solution of sodium salt of 4-(piperazin-1-yl)benzoic acid (0.36g, 1.5 mmol) and potassium carbonate (0.20g,1.5mmol) in 3mL of water di-tert-butyl dicarbonate (0.32g, 1.5 mmol) was added as a solution in 1.8mltetrahydrofuran, dropwise at 0 °C. After the addition was completed, the reaction mixture was allowed to cometo room temperature and stirred for 4 h. THF was removed in vacuum and the aqueous phase was washed withether. The aqueous phase was separated and adjusted to pH 2 with 1 N hydrochloric acid, and extracted with ethylacetate. The combined organic extracts were concentrated to get 4-(4-(tert-butoxycarbonyl)piperazin-1-yl)benzoic acid (0.13 g, 45percent) as a white solid.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 15, p. 3754 - 3760
  • 4
  • [ 57260-71-6 ]
  • [ 162046-66-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 3, p. 1165 - 1181
[2] Patent: US2012/114600, 2012, A1,
[3] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 6, p. 629 - 634
[4] Molecular Pharmacology, 2016, vol. 90, # 2, p. 80 - 95
[5] Patent: US2018/141923, 2018, A1,
  • 5
  • [ 451-46-7 ]
  • [ 162046-66-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 3, p. 1165 - 1181
[2] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 7, p. 2089 - 2108
[3] Patent: US2012/114600, 2012, A1,
[4] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 6, p. 629 - 634
  • 6
  • [ 80518-57-6 ]
  • [ 162046-66-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 7, p. 2089 - 2108
  • 7
  • [ 163210-97-7 ]
  • [ 162046-66-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 15, p. 4646 - 4661
  • 8
  • [ 619-45-4 ]
  • [ 162046-66-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 15, p. 4646 - 4661
  • 9
  • [ 403-33-8 ]
  • [ 162046-66-4 ]
Reference: [1] Molecular Pharmacology, 2016, vol. 90, # 2, p. 80 - 95
  • 10
  • [ 619-42-1 ]
  • [ 162046-66-4 ]
Reference: [1] Patent: US2018/141923, 2018, A1,
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