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[ CAS No. 39499-34-8 ] {[proInfo.proName]}

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Chemical Structure| 39499-34-8
Chemical Structure| 39499-34-8
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Product Details of [ 39499-34-8 ]

CAS No. :39499-34-8 MDL No. :MFCD00085127
Formula : C5H4ClNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :XMVNMWDLOGSUSM-UHFFFAOYSA-N
M.W : 145.54 Pubchem ID :2736894
Synonyms :

Safety of [ 39499-34-8 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P301+P330+P331-P302+P352-P304+P340-P305+P351+P338-P310 UN#:3265
Hazard Statements:H314 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 39499-34-8 ]

* 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.

  • Downstream synthetic route of [ 39499-34-8 ]

[ 39499-34-8 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 6789-94-2 ]
  • [ 39499-34-8 ]
  • [ 108-20-3 ]
  • N-(1-ethyl-3-piperidinyl)-5-methylisoxazole-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
50.3% With sodium hydroxide; In dichloromethane; water; Petroleum ether; Example 3 Preparation of N-(1-ethyl-3-piperidinyl)-5-methylisoxazole-3carboxamide (compound No. 14) To a solution of <strong>[6789-94-2]3-amino-N-ethylpiperidine</strong> (4.61 g; 36 mmols) in methylene chloride (20 ml) and water (10 ml), a solution of 5-methyl-3-isoxazole-carbonyl chloride (5.68 g; 39 mmols) in methylene chloride (35 ml) and 1N NaOH (39 ml) were added contemporaneously at the temperature of 3C. After 30 minutes the temperature was allowed to raise to the room value and after 1-3 h the phases were separated; the aqueous phase was extracted again with methylene chloride. After drying and evaporation of the solvent, a crude product (7.1 g) was obtained which was then crystallyzed from a mixture of isopropyl ether/petroleum ether (ratio 1:1; 160 ml). N-(1-ethyl-3-piperidinyl)-5-methylisoxazole-3-carboxamide was obtained (4.3 g; yield 50.3%) m.p. 84-86C. 1H-NMR (200 MHz, CDCl3): delta (ppm): 1.04 (t, 3H, C H 3-CH2); 1.51-2.61 (m, 8H); 2.38 (q, 2H, CH3-C H 2); 2.46 (d, 1H, CH3-C); 4.20 (m, 1H, CH-N); 6.41 (q, 1H, CH=C); 7.29 (d, 1H, NH).
50.3% With sodium hydroxide; In dichloromethane; water; Petroleum ether; EXAMPLE 3 Preparation of N-(1-ethyl-3-piperidinyl)-5-methylisoxazole-3-carboxamide (compound No. 14) To a solution of <strong>[6789-94-2]3-amino-N-ethylpiperidine</strong> (4.61 g; 36 mmols) in methylene chloride (20 ml) and water (10 ml), a solution of 5-methyl-3-isoxazole-carbonyl chloride (5.68 g; 39 mmols) in methylene chloride (35 ml) and 1N NaOH (39 ml) were added contemporaneously at the temperature of 3 C. After 30 minutes the temperature was allowed to raise to the room value and after 1-3 h the phases were separated; the aqueous phase was extracted again with methylene chloride. After drying and evaporation of the solvent, a crude product (7.1 g) was obtained which was then crystallyzed from a mixture of isopropyl ether/petroleum ether (ratio 1:1; 160 ml). N-(1-ethyl-3-piperidinyl)-5-methylisoxazole-3-carboxamide was obtained (4.3 g; yield 50.3%) m.p. 84-86 C. 1 H--NMR (200 MHz, CDCl3): delta (ppm): 1.04 (t, 3H, CH3 --CH2); 1.51-2.61 (m, 8H); 2.38 (q, 2H, CH3 --CH2); 2.46 (d, 1H, CH3 --C); 4.20 (m, 1H, CH--N); 6.41 (q, 1H, CH=C); 7.29 (d, 1H, NH).
  • 2
  • [ 39499-34-8 ]
  • [ 873-95-0 ]
  • [ 1377150-73-6 ]
YieldReaction ConditionsOperation in experiment
35% General procedure; To a 250 mL single neck flask equipped with a ST "Y" tube, condenser and a pressure equalizing dropping funnel containing 85 mL of anhydrous THF, was cautiously added NaH (0.84 g, 35.0 mmol) with constant stirring, maintaining the temperature below 20 C with external cooling. After the reaction, 14b (1.9 g, 15.0 mmol) was added over 30 min through the "Y" tube, and after the addition, a further 10 mL of THF washed the "Y" tube. The reaction mixture was heated to reflux for 20 min, cooled to room temperature and 5-methylisoxazolyl carbonylchloride [7] (2.30 g, 16.0 mmol) in anhydrous THF (25 mL) was added dropwise over 5 min. After stirring at room temperature for a further 10 min, the mixture was quenched with water and transferred to a 250 mL Erlenmeyer flask, neutralized with concentrated HCl (～10 mL), diluted with dichloromethane (55 mL) and transferred to a separatory funnel. The aqueous layer was discarded and the organic layer was washed successively with water (55 mL), 10% NaHCO3 (2 × 55 mL), and water (55 mL). The organic layer was dried over sodium sulfate, evaporated in vacuo and the residue triturated with anhydrous Et2O (110 mL). The crude solid was recrystallized from EtOAc, to give 15b (0.75 g 21%) as cream colored crystals.
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