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[ CAS No. 60437-30-1 ]

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2D
Chemical Structure| 60437-30-1
Chemical Structure| 60437-30-1
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Product Details of [ 60437-30-1 ]

CAS No. :60437-30-1MDL No. :MFCD17453986
Formula : C14H19NO3 Boiling Point : -
Linear Structure Formula :-InChI Key :-
M.W :249.31Pubchem ID :12343427
Synonyms :

Computed Properties of [ 60437-30-1 ]

TPSA : 49.8 H-Bond Acceptor Count : 4
XLogP3 : 1.3 H-Bond Donor Count : 1
SP3 : 0.50 Rotatable Bond Count : 4

Safety of [ 60437-30-1 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P280-P305+P351+P338UN#:N/A
Hazard Statements:H302Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 60437-30-1 ]

  • Upstream synthesis route of [ 60437-30-1 ]
  • Downstream synthetic route of [ 60437-30-1 ]

[ 60437-30-1 ] Synthesis Path-Upstream   1~6

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YieldReaction ConditionsOperation in experiment
90%
Stage #1: at 90℃; for 1 h;
Stage #2: at 50℃; for 1 h;
Example 1A
Methyl 1-benzyl-4-hydroxypiperidine-4-carboxylate
A solution of 10.52 g (48.64 mmol) of 1-benzyl-4-hydroxypiperidine-4-carbonitrile in 60 ml of conc. hydrochloric acid is stirred for one hour at 90° C.
The reaction solution is concentrated on a rotary evaporator and dried under high vacuum.
The residue obtained is taken up in 150 ml of methanol, 6 ml of conc. sulfuric acid are added and the mixture stirred for 1 hour at 50° C.
After cooling the reaction mixture is diluted with ethyl acetate and rendered alkaline with a saturated sodium carbonate solution.
The organic phase is washed with a sodium chloride solution, dried over sodium sulfate and concentrated on a rotary evaporator. 10.8 g (43.6 mmol, 90percent th.) of product are obtained. LC-MS (method 4): Rt=2.08 min. MS (ESIpos): m/z=250 (M+H)+ 1H NMR (400 MHz, DMSO-d6): δ=7.35-7.2 (m, 5H), 5.28 (s, 1H), 3.63 (s, 3H), 3.45 (s, 2H), 2.53-2.4 (m, 2H, partly masked by DMSO), 2.38-2.2 (m, 2H), 1.9-1.78 (m, 2H), 1.59 (d, 2H).
62.5% With hydrogenchloride In water at 85℃; for 18 h; Intermediate: methyl 1-benzyl-4-hydroxypiperidine-4-carboxylate
A stirred mixture of 1-benzyl-4-hydroxypiperidine-4-carbonitrile (2 g, 9.25 mmol) in MeOH (12 mL) and conc. HCl (12 mL, 144 mmol) was heated at 85° C. for 18 h.
The reaction mixture was cooled to rt, then concentrated and neutralized with 1 N NaOH, extracted with 2*EtOAc, then the combined organic phase was washed with sat. NaCl, dried (Na2SO4).
The crude product was purified by silica gel (0-100percent EtOAC in hexane) to yield methyl 1-benzyl-4-hydroxypiperidine-4-carboxylate (1.44 g, 5.78 mmol, 62.5percent yield). LC/MS (Cond. N-1): [M+H]+ 250.15, RT=1.70 min. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.37-7.29 (m, 4H), 7.28-7.22 (m, 1H), 3.82-3.73 (m, 3H), 3.54 (s, 2H), 2.78-2.68 (m, 2H), 2.40 (td, J=11.9, 2.6 Hz, 2H), 2.12 (td, J=12.7, 4.6 Hz, 2H), 1.62 (dq, J=13.8, 2.8 Hz, 2H).
11.2 g
Stage #1: With hydrogenchloride; water In acetic acid for 3 h; Reflux
Stage #2: With sulfuric acid In acetic acid for 12 h; Reflux
[00206] A solution of sodium metabisulfate (14.5 g, 0.075 mol) in distilled water (60 mL) was added over 2h to a stuffed mixture of 1 (23.2 g, 123 mmol), potassium cyanide (9.9 g, 153 mmol), and water (60 mL). The mixture was stuffed at 25°C for 5 hours. The mixture was extracted with ethyl acetate (2 x 100 mL) and the organics dried (MgSO4), and concentrated to give an oil which slowly solidified on standing at RT. The waxy solid was triturated with hexanes-ether (9:1) and filtered to give 14.9 g of the corresponding cyanohydrin. This solid was dissolved in acetic acid (25 mL) and the solution was diluted with concentrated HC1 (75 mL). The solution was refluxed for 3 hours and concentrated to a solid mass. Toluene (100 mL) was added to the solid mass and the mixture was evaporated. This process was repeated one additional time. The resulting solid was then diluted with MeOH (100 mL) and treated with concentrated sulfuric acid (3.4 g). The solution was refluxed for 12 hours and concentrated to an oily residue which was diluted with a saturated solution of sodium bicarbonate (100 mL) and then extracted with EtOAc (2 x 100 mL). The organics were dried (MgSO4), filtered, concentrated, and chromatographed on silica gel (60percent hexanes 40percent EtOAc) to give 2 (11.2 g) as an amber oil.
6.2 g
Stage #1: at 90℃; for 1 h;
Stage #2: at 50℃; for 1 h;
[0609] l-Benzyl-4-hydroxypiperidine-4-carbomtrile (10.0 g) was added to concentrated hydrochloric acid (25 mL), and the resultant was stirred for 1 hour at 90°C. The reaction mixture was cooled to room temperature, and it was concentrated under reduced pressure. Toluene was added to the residue, and the resultant was again concentrated. Concentrated sulfuric acid (4.00 mL) was added to a solution of the obtained residue in methanol (100 mL), and the resultant was stirred for 1 hour at 50°C. The reaction mixture was cooled to room temperature, it was neutralized by the addition of sodium hydrogen carbonate, and then insoluble matter was separated by filtration. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by a silica gel column chromatography ( , hexane/ethyl acetate), thereby obtaining the title compound (6.20 g). MS (ESI+): [M+H]+ 250.2.

Reference: [1] Patent: US2010/22527, 2010, A1, . Location in patent: Page/Page column 16
[2] Patent: US2017/107202, 2017, A1, . Location in patent: Paragraph 0395; 0396
[3] Journal of Medicinal Chemistry, 1993, vol. 36, # 16, p. 2292 - 2299
[4] Patent: US2005/9841, 2005, A1, . Location in patent: Page/Page column 18
[5] Patent: WO2013/106717, 2013, A1, . Location in patent: Paragraph 00206
[6] Patent: WO2014/142363, 2014, A1, . Location in patent: Paragraph 0609
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Reference: [1] Patent: US2005/80095, 2005, A1, . Location in patent: Page/Page column 20
[2] Patent: US9156825, 2015, B2,
  • 3
  • [ 67-56-1 ]
  • [ 59119-18-5 ]
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YieldReaction ConditionsOperation in experiment
11.2 g for 12 h; Reflux A solution of sodium metabisulfate (14.5 g, 0.075 mol) in distilled water (60 mL) was added over 2h to a stirred mixture of 1 (23.2 g, 123 mmol), potassium cyanide (9.9 g, 153 mmol), and water (60 mL). The mixture was stirred at 25° C. for 5 hours. The mixture was extracted with ethyl acetate (2×100 mL) and the organics dried (MgSO4), and concentrated to give an oil which slowly solidified on standing at RT. The waxy solid was triturated with hexanes-ether (9:1) and filtered to give 14.9 g of the corresponding cyanohydrin. This solid was dissolved in acetic acid (25 mL) and the solution was diluted with concentrated HCl (75 mL). The solution was refluxed for 3 hours and concentrated to a solid mass. Toluene (100 mL) was added to the solid mass and the mixture was evaporated. This process was repeated one additional time. The resulting solid was then diluted with MeOH (100 mL) and treated with concentrated sulfuric acid (3.4 g). The solution was refluxed for 12 hours and concentrated to an oily residue which was diluted with a saturated solution of sodium bicarbonate (100 mL) and then extracted with EtOAc (2×100 mL). The organics were dried (MgSO4), filtered, concentrated, and chromatographed on silica gel (60percent hexanes/40percent EtOAc) to give 2 (11.2 g) as an amber oil.
Reference: [1] Patent: US9156825, 2015, B2, . Location in patent: Page/Page column 67
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Reference: [1] Patent: EP1221441, 2002, A2, . Location in patent: Page 201-202
  • 5
  • [ 3612-20-2 ]
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Reference: [1] Patent: WO2013/106717, 2013, A1,
[2] Patent: US9156825, 2015, B2,
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  • [ 60437-30-1 ]
  • [ 92197-36-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1988, vol. 31, # 2, p. 486 - 491
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