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Chemical Structure| 498-94-2 Chemical Structure| 498-94-2
Chemical Structure| 498-94-2

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Isonipecotic acid is a specific GABAA receptor agonist.

Synonyms: 4-Piperidinecarboxylic acid; 4-Carboxypiperidine; Hexahydroisonicotinic acid

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Product Details of Isonipecotic acid

CAS No. :498-94-2
Formula : C6H11NO2
M.W : 129.16
SMILES Code : O=C(C1CCNCC1)O
Synonyms :
4-Piperidinecarboxylic acid; 4-Carboxypiperidine; Hexahydroisonicotinic acid
MDL No. :MFCD00006004
InChI Key :SRJOCJYGOFTFLH-UHFFFAOYSA-N
Pubchem ID :3773

Safety of Isonipecotic acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Isonipecotic acid

* 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 [ 498-94-2 ]
  • Downstream synthetic route of [ 498-94-2 ]

[ 498-94-2 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 498-94-2 ]
  • [ 1690-75-1 ]
References: [1] Journal of Medicinal Chemistry, 1988, vol. 31, # 4, p. 807 - 814.
  • 2
  • [ 498-94-2 ]
  • [ 55695-51-7 ]
References: [1] Farmaco, Edizione Scientifica, 1957, vol. 12, p. 853,862.
  • 3
  • [ 498-94-2 ]
  • [ 541-41-3 ]
  • [ 118133-15-6 ]
YieldReaction ConditionsOperation in experiment
92% With sodium hydroxide In water at 0 - 30℃; for 3 h; Example 1 — Preparation of 1-(Ethoxycarbonyl) piperidine-4-Carboxylic AcidTo a solution of (154.8 gm) Sodium hydroxide in (750 ml) purified water, Isonipecotic acid(250gm) was added at 0-10°C, followed by the slow addition of ethyl chloroformate (231 ml) at 5-20°C. The reaction mixture was heated to 20-30°C and maintained for 3 hrs at the sametemperature. After completion of the reaction, the reaction mass was acidified to a pH 1-2 byaddition of hydrochloric acid. Then toluene (750 ml) was added to the reaction mass and stirred for15 minutes at 25-30 °C. The organic layer was separated and concentrated under vacuum at below70°C to obtain a residue. The resi4ue_was_mixed. with cyclohexane (1250 ml) at 60-70°C, thencooled to 25-30°C and maintain for I hour at the same temperature. The resulted contents werefiltered, and washed with cyclohexane (1250 ml) and dried at 50-55°C. Percentage Yield: 92percent
91.9% With sodium carbonate In tetrahydrofuran; water at 20℃; for 2 h; 5.16 g (40 mmol) of the starting material 4-piperidinecarboxylic acid was added to a 100 ml round bottom flask, Na2CO3 5.04 g (48 mmol) and 40 mL of water was added. 5.13 g (48 mmol) was dissolved in 40 mL of tetrahydrofuran, added dropwise to a round bottom flask and stirred at room temperature for 2 h. The reaction was evaporated to remove tetrahydrofuran rotary end, was added 60mL of water, adjusted to pH 2 with 2MHCl, extracted with EA (30mL × 3), combined EA phases were dried over anhydrous MgSO4, filtered and rotary-dry products acquired Intermediate 1 as a white solid. Yield 91.9percent.
References: [1] Patent: WO2014/83571, 2014, A1, . Location in patent: Page/Page column 17.
[2] Journal of Medicinal Chemistry, 2017, vol. 60, # 11, p. 4680 - 4692.
[3] Patent: CN103694242, 2016, B, . Location in patent: Paragraph 0069; 0070.
[4] Patent: US5663200, 1997, A, .
[5] Archiv der Pharmazie, 2016, p. 614 - 626.
 

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