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[ CAS No. 68947-43-3 ]

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Chemical Structure| 68947-43-3
Chemical Structure| 68947-43-3
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CAS No. :68947-43-3 MDL No. :MFCD06659473
Formula : C7H13NO2 Boiling Point : 246.1°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :143.18 g/mol Pubchem ID :2736939
Synonyms :

Safety of [ 68947-43-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 68947-43-3 ]

  • Upstream synthesis route of [ 68947-43-3 ]
  • Downstream synthetic route of [ 68947-43-3 ]

[ 68947-43-3 ] Synthesis Path-Upstream   1~15

  • 1
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  • [ 50-00-0 ]
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YieldReaction ConditionsOperation in experiment
98.1% With hydrogen In water at 16 - 25℃; Load isonipicotic acid (1 kg, 7.74 mol), water (10 L), formaldehyde (37percent solution in water, 720 g, 8.87 mol, 1.15 eq. ) and wet Pd/C catalyst (10percent; 55percent paste, 100 g) into a stainless steel hydrogenation reactor. Pressurize the reactor with H2 (3 bar) and stir the reaction mixture overnight at 200-300 rpm at 16-25°C. Stop the reaction and filter off the catalyst. Wash the filtrate with water (500 ml) and concentrate under vacuum. Distill off the remaining water from the residue using ethanol (2x 1 L). Dry the solid overnight under vacuum at 50°C to obtain the title product as an off-white solid (1087 g, 98. 1percent yield).
76% With hydrogen In water at 20℃; for 18 h; Isonipecotic acid (50 g, 0.387 mole) was dissolved in water (500 ml) and 37percent formaldehyde (125 ml). 10percent Palladium on carbon (50 g) was added and the mixture was shaken under a hydrogen atmosphere at 60 psi at room temperature for 18 hours. [00375] The catalyst was filtered, washed with water, and the filtrate was concentrated under reduced pressure. The residue was slurried in water and concentrated in vacuo. The residue was slurried in ethanol and concentrated in vacuo to give a white solid. Drying under vacuum at ambient temperature for 18 h gave 42.2 g (76percent) of a white solid, [00376] mp 173-5° C. MS(m/e): 143 (M+). [00377] Analysis for C7H13NO2: [00378] Calcd: C, 58.72; H, 9.15; N, 9.78; Found: C, 58.24; H, 9.59; N. 9.71.
18% for 20 h; Heating / reflux Reference Example 249: l-MethvI-piperidine-4-carboxylic acid . A solution of 4-piperidine carboxylic acid (1.0 g, 7.75 mmol) in a mixture of90percent formic acid (3 mL) and 37percent formaldehyde solution (2 mL) was heated at reflux for 20 h. The volatiles were removed in vacuo and cone. HCl added to the residue. The reaction mixture was extracted with dichloromethane and washed with brine solution. The organic layer was dried over sodium sulfate, filtered and dried to afford 1-methyl- piperidine-4-carboxylic acid (0.20 g, 18 percent).
Reference: [1] Patent: WO2003/84949, 2003, A1, . Location in patent: Page/Page column 45; 46
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 10118 - 10129
[3] Patent: US6777428, 2004, B1, . Location in patent: Page column 24
[4] Journal of Medicinal Chemistry, 1993, vol. 36, # 4, p. 449 - 459
[5] Patent: WO2008/62182, 2008, A1, . Location in patent: Page/Page column 161-162
[6] Journal of the American Chemical Society, 1949, vol. 71, p. 2825
[7] Patent: US2833775, 1955, ,
[8] Journal of Labelled Compounds and Radiopharmaceuticals, 1995, vol. 36, # 2, p. 193 - 204
[9] Patent: US2011/190299, 2011, A1, . Location in patent: Page/Page column 21
  • 2
  • [ 24252-37-7 ]
  • [ 68947-43-3 ]
YieldReaction ConditionsOperation in experiment
1.79 g With sodium hydroxide In water at 20℃; (0550) A mixture of ethyl piperidine-4-carboxylate (4.72 g), methyl iodide (2.24 mL), potassium carbonate (8.29 g) and acetonitrile (50 mL) was stirred at room temperature for 2 hrs. The reaction mixture was concentrated under reduced pressure and water (150 mL) was added. The mixture was extracted with ethyl acetate (150 mL). The ethyl acetate layer was washed with saturated brine (100 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. A 1N aqueous sodium hydroxide solution (20 mL) was added to the residue (2.64 g), and the mixture was stirred overnight at room temperature. The reaction mixture was neutralized by adding 1N hydrochloric acid (20 mL) and the mixture was concentrated under reduced pressure. Ethanol was added to the residue, and the precipitate was filtered off. The filtrate was concentrated under reduced pressure. This step was repeated and ethanol and ethyl acetate were added to the residue for crystallization to give 1-methylpiperidine-4-carboxylic acid (1.79 g) as a colorless solid. (0551) 1H-NMR (CD3OD): 1.80-1.98 (2H, m), 2.00-2.14 (2H, m), 2.28-2.42 (1H, m), 2.78 (3H, s), 2.88-3.04 (2H, m), 3.32-3.44 (2H, m).
Reference: [1] Patent: US6569854, 2003, B1,
[2] Patent: EP1602362, 2005, A1, . Location in patent: Page/Page column 60
[3] Patent: EP1607088, 2005, A1, . Location in patent: Page/Page column 59
[4] Patent: US2016/128945, 2016, A1, . Location in patent: Paragraph 0550; 0551
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  • [ 74-88-4 ]
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Reference: [1] Patent: WO2003/105845, 2003, A1, . Location in patent: Page 104-106
  • 4
  • [ 946493-45-4 ]
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Reference: [1] Patent: US2010/234405, 2010, A1, . Location in patent: Page/Page column 6
  • 5
  • [ 20691-89-8 ]
  • [ 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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  • [ 5746-18-9 ]
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Reference: [1] Journal of the American Chemical Society, 1959, vol. 81, p. 1201
  • 7
  • [ 55-22-1 ]
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Reference: [1] Journal of the American Chemical Society, 1959, vol. 81, p. 1201
[2] Patent: US2833775, 1955, ,
  • 8
  • [ 824-77-1 ]
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Reference: [1] Collection of Czechoslovak Chemical Communications, 1954, vol. 19, p. 949,951
  • 9
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Reference: [1] Patent: US2016/128945, 2016, A1,
  • 10
  • [ 1690-75-1 ]
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Reference: [1] Helvetica Chimica Acta, 1954, vol. 37, p. 1672,1676
  • 11
  • [ 2459-09-8 ]
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Reference: [1] Helvetica Chimica Acta, 1954, vol. 37, p. 1672,1676
  • 12
  • [ 7630-02-6 ]
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Reference: [1] Helvetica Chimica Acta, 1954, vol. 37, p. 1672,1676
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  • [ 64-18-6 ]
  • [ 590-29-4 ]
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Reference: [1] Collection of Czechoslovak Chemical Communications, 1954, vol. 19, p. 949,951
  • 14
  • [ 68947-43-3 ]
  • [ 24252-37-7 ]
YieldReaction ConditionsOperation in experiment
50% With hydrogenchloride; sodium hydrogencarbonate In 1,4-dioxane; dichloromethane a)
A solution of 2N hydrochloric acid in dioxane (2.8 ml, 11.13 mmol) was added to 1-methyl-4-piperdine carboxylic acid (20 g, 111.33 mmol) and the mixture heated at reflux for 18 hours.
The reaction was concentrated to dryness and the resultant solid dissolved in dichloromethane and washed with a saturated solution of sodium bicarbonate, dried (magnesium sulphate) and concentrated to afford 1-methyl-4-piperdine carboxylic acid ethyl ester as a white solid (9.52 g, 50percent yield).
Reference: [1] Patent: US7235559, 2007, B1,
[2] Collection of Czechoslovak Chemical Communications, 1954, vol. 19, p. 949,951
[3] Helvetica Chimica Acta, 1954, vol. 37, p. 1762,1765
  • 15
  • [ 68947-43-3 ]
  • [ 6638-79-5 ]
  • [ 215950-19-9 ]
YieldReaction ConditionsOperation in experiment
80%
Stage #1: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethyl-formamide) for 63 h;
Stage #2: With sodium hydroxide In water
1-Methylisonipecotic acid (5.5 g, 38.4 mmol) was dissolved in dimethylformamide (100 ml) with heating. Diisopropylethylamine (8.0 ml, 46.1 mmol), 1-hydroxybenzotriazole (5.2 g, 38.4 mmol), and N,O-dimethylhydroxylamine hydrochloride (4.1 g, 42.2 mmol) were added and the reaction mixture was stirred 5 min. 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (7.4 g, 38.4 mmol) was added and the resulting homogeneous solution was stirred for 63 hours at ambient temperature. The solvent was removed under reduced pressure. The residue was dissolved in water and the solution was basified to pH 9 with 5N sodium hydroxide solution. This aqueous solution was extracted with methylene chloride then saturated with sodium chloride and extracted with chloroform/isopropanol (3/1). The combined organic extracts were dried over sodium sulfate and the solvent was removed under reduced pressure to give 9.5 g of a yellow liquid. Purification by flash chromatography (silica gel, methylene chloride:methanol:ammonium hydroxide, 100:10:1) gave 5.7 g (80percent) of product as a light yellow liquid. [00381] MS (m/e): 186(M+). [00382] Analysis for C9H18N2O2:
Reference: [1] Patent: US6777428, 2004, B1, . Location in patent: Page column 24-25
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