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[ CAS No. 10315-06-7 ]

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Chemical Structure| 10315-06-7
Chemical Structure| 10315-06-7
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CAS No. :10315-06-7 MDL No. :MFCD09750949
Formula : C14H19NO2 Boiling Point : 310.7°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :233.31 g/mol Pubchem ID :11436222
Synonyms :

Safety of [ 10315-06-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H302-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 10315-06-7 ]

  • Upstream synthesis route of [ 10315-06-7 ]
  • Downstream synthetic route of [ 10315-06-7 ]

[ 10315-06-7 ] Synthesis Path-Upstream   1~9

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YieldReaction ConditionsOperation in experiment
88% With triethylamine In chloroform at 20℃; To A solution of METHYL PIPERIDINE-4-CARBOXYLATE (10. 00 G, 6. 4 MMOL) AND triethylamine (10. 32 G, 10. 2 MMOL) IN CHC13 (100 ML), BENZYL BROMIDE (14. 69 G, 8. 6 mmol) was added under argon atmosphere while cooling with a water and ice bath. The mixture was stirred at room temperature overnight. CHCI3 and water were added and the two phases were separated. The aqueous phase was extracted with CHCI3. The organic phase was dried over NA2S04 and concentrated to dryness, to afford 13. 80 G OF THE DESIRED COMPOUND AS AN ORANGE solid (YIELD : 88percent)
78% With potassium carbonate In acetonitrile at 85℃; Inert atmosphere General procedure: A mix of methyl piperidine-4-carboxylate or ethyl 2-(piperidin-4-yl)acetate (10 mmol) in acetonitrile (20 ml), 1a–j (11 mmol),anhydrous K2CO3 (12 mmol) was refluxed under nitrogen for 8 hat 85 C. The mixture was then cooled and filtered and the solvent removed in vacuum. The residue was dissolved in ethyl acetate(50 ml) and washed with water (15 ml). Drying and removal of the solvent followed by chromatography (ethyl acetate/petroleumether = 1:4) afforded desired product 2a–j.
Reference: [1] Arkivoc, 2010, vol. 2010, # 10, p. 132 - 148
[2] Patent: WO2004/76450, 2004, A1, . Location in patent: Page 43-44
[3] Synthesis, 2002, # 7, p. 911 - 915
[4] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 18, p. 4324 - 4338
  • 2
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YieldReaction ConditionsOperation in experiment
98.6% With triethylamine In 1,2-dichloro-ethane at 10 - 20℃; for 1.5 h; Reflux; Large scale In the 1000L reactor, 360 kg of 1,2-dichloroethane was recovered in Example 2, and 69.54 kg of new 1,2-dichloroethane was added.Under stirring, 143.18 kg of methyl piperidinecarboxylate and 121.43 kg of triethylamine were added, and benzyl chloride 139.24 kg was added dropwise at a temperature of 10 to 20°C.After the dripping is completed, the temperature is gradually raised to reflux for 1.5 hours. The reaction of the raw material is completely cooled to 20 to 30° C., and 150 kg of water is added for 30 minutes to separate the liquid.The organic layer was dried, filtered, and the filtrate was concentrated to obtain 230.04 kg of methyl N-benzyl-4-piperidinecarboxylate;The molar yield was 98.6percent and the purity was 99.61percent.The 1,2-dichloroethane was recovered for the next reaction.
Reference: [1] Patent: CN107903206, 2018, A, . Location in patent: Paragraph 0022; 0023; 0024; 0025
[2] Patent: WO2008/31227, 2008, A1, . Location in patent: Page/Page column 37
[3] ChemSusChem, 2016, vol. 9, # 1, p. 67 - 74
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YieldReaction ConditionsOperation in experiment
96.5% With sodium hydrogencarbonate In ethanol for 3 h; Reflux; Large scale The 1.62kg4- piperidine carboxylic acid methyl ester hydrochloride, 1.08kg, put benzyl chloride, 1.89kg and 4.3kg of sodium bicarbonate was added to the ethanol 20L reactor, heated to reflux and maintained at reflux the reaction 3h, cooled to an inner temperature of 30 about deg.] C, discharge, filtered, and the filter cake washed with ethanol 2.15kg, drained, the filtrate was concentrated paste, the residue is dispersed in 4.7kg of toluene and 6.0kg of pure water, the organic layer was washed with stirring, separate the organic layer, the toluene was concentrated to give 1-benzyl-4-piperidine carboxylic acid methyl ester 1.92kg, as a pale yellow oily liquid. Yield: 96.5percent (in terms benzyl chloride). HPLC: 99.12percent
Reference: [1] Patent: CN105693596, 2016, A, . Location in patent: Paragraph 0040; 0041; 0042; 0043
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Reference: [1] Journal of Medicinal Chemistry, 1999, vol. 42, # 26, p. 5359 - 5368
[2] Patent: US2009/124624, 2009, A1, . Location in patent: Page/Page column 16-17
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Reference: [1] ChemSusChem, 2016, vol. 9, # 1, p. 67 - 74
[2] ChemSusChem, 2016, vol. 9, # 1, p. 67 - 74
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Reference: [1] Journal of the American Chemical Society, 1959, vol. 81, p. 704,707
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Reference: [1] Synthesis (Germany), 2015, vol. 47, # 23, p. 3758 - 3766
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  • [ 10315-07-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 18, p. 4324 - 4338
  • 9
  • [ 10315-06-7 ]
  • [ 80845-58-5 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 18, p. 5875 - 5878
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