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Chemical Structure| 19718-92-4 Chemical Structure| 19718-92-4

Structure of 19718-92-4

Chemical Structure| 19718-92-4

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Product Details of [ 19718-92-4 ]

CAS No. :19718-92-4
Formula : C8H19NO2
M.W : 161.24
SMILES Code : CN(C)CCCC(OC)OC
MDL No. :MFCD06411126

Safety of [ 19718-92-4 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H314-H226
Precautionary Statements:P501-P270-P240-P210-P233-P243-P241-P242-P264-P280-P370+P378-P303+P361+P353-P301+P330+P331-P363-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P403+P235-P405
Class:8(3)
UN#:2920
Packing Group:

Application In Synthesis of [ 19718-92-4 ]

* 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 [ 19718-92-4 ]

[ 19718-92-4 ] Synthesis Path-Downstream   1~6

  • 2
  • [ 19718-92-4 ]
  • (4-[1,2,4]triazol-1-ylmethylphenyl)hydrazine hydrochloride [ No CAS ]
  • [ 144034-80-0 ]
  • 3
  • 1-(4-hydrazinophenyl)-methyl-1,2,4-triazole dihydrochloride [ No CAS ]
  • [ 19718-92-4 ]
  • [ 144034-80-0 ]
YieldReaction ConditionsOperation in experiment
In aqueous sulphuric acid; ethyl acetate; EXAMPLE 17 N,N-Dimethyl-2-[5-(1,2,4-triazol-1ylmethyl)-1H-indol-3-yl]ethylamine. Succinate. Procedure B A solution of 1-(4-hydrazinophenyl)methyl-1,2,4-triazole dihydrochloride (2 g, 7.6 mmol, Example 5 step 3) and 4-N,N-dimethylaminobutanal dimethylacetal (1.8 g, 11.2 mmol) in 4% aqueous sulphuric acid (70 ml) was heated at reflux for 2 h. After the reaction mixture was cooled to room temperature, ethyl acetate (200 ml) was added and the aqueous basified with K2 CO3. The aqueous was separated and extracted further with ethyl acetate (2*150 ml). The combined organics were dried (Na2 SO4) and evaporated, and the residue chromatographed on silica gel eluding with CH2 Cl2 /EtOH/NH3 (30:8:1) to give the title-triazole (610 mg, 30%). The succinate salt was prepared by addition of a solution of succinic acid (0.27 g, 2.3 mmol) in methanol (3 ml) to a solution of the triazole (0.61 g, 2.3 mmol) in methanol (5 ml).
  • 4
  • 1-(4-aminophenyl)methyl-1,2,4-triazole dihydrochloride [ No CAS ]
  • [ 19718-92-4 ]
  • [ 144034-80-0 ]
YieldReaction ConditionsOperation in experiment
35% hydrogenchloride; In N,N-dimethyl-formamide; at 80 - 85℃;Product distribution / selectivity; EXAMPLE 5; Experiments were carried out using the general procedure of Example 1 , with different acid catalysts under aqueous and nonaqueous conditions, to determine influences on the yield and quality of the rizatriptan base product. As the dimer impurity was a major potential impurity formed during the process, quality of product was monitored with respect to the percentage of dimer impurity in the product. The results of the experiments are tabulated below:
25% hydrogenchloride; In methanol; at 70 - 75℃;Product distribution / selectivity; EXAMPLE 5; Experiments were carried out using the general procedure of Example 1 , with different acid catalysts under aqueous and nonaqueous conditions, to determine influences on the yield and quality of the rizatriptan base product. As the dimer impurity was a major potential impurity formed during the process, quality of product was monitored with respect to the percentage of dimer impurity in the product. The results of the experiments are tabulated below:
< 10% zinc(II) chloride; at 100 - 120℃;Product distribution / selectivity; EXAMPLE 5; Experiments were carried out using the general procedure of Example 1 , with different acid catalysts under aqueous and nonaqueous conditions, to determine influences on the yield and quality of the rizatriptan base product. As the dimer impurity was a major potential impurity formed during the process, quality of product was monitored with respect to the percentage of dimer impurity in the product. The results of the experiments are tabulated below:
  • 5
  • 1-(4-aminophenyl)methyl-1,2,4-triazole dihydrochloride [ No CAS ]
  • [ 19718-92-4 ]
  • 3-[[3-[2-(N,N-dimethylamino)ethyl]-2-[[3-[2-(N,N-dimethylamino)ethyl]-1H-indol-5-yl]methyl]-1H-indol-5-yl]methyl]-1H-1,2,4-triazole [ No CAS ]
  • [ 144034-80-0 ]
YieldReaction ConditionsOperation in experiment
75.59 - 77.46% hydrogenchloride; In water; at 0 - 75℃; for 3 - 4h;Product distribution / selectivity; EXAMPLE 1; PREPARATION OF RIZATRIPTAN BASE; To a solution of 200 g of 1-(4-aminophenyl) methyl-1 ,-2,4 triazole dihydrochloride in 2000 ml water was added 158 ml concentrated hydrochloric acid and 180.4 g of 4-dimethyl-amino-butanal-dimethyl-acetal, and the mixture was maintained for 1 hour at 4-5 C. Another 158 ml of concentrated hydrochloric acid was added to the mixture and the mixture was heated to 70-75 C for 2 hours. The mixture was cooled to 25-30 C, quenched by adding 260 ml of 40% aqueous sodium hydroxide solution, and the mixture was extracted with 3000 ml of ethyl acetate three times. The combined organic layer was passed through 840 g of silica gel (100-200 mesh) packed in a glass column. The silica gel was eluted with 8000 ml of isopropanol. Solvent was evaporated from the eluate to yield 108 g of the desired purified rizatriptan base having a dimer impurity content of 0.095 area-% as measured by HPLC. EPO <DP n="13"/>-; EXAMPLE 2; PREPARATION OF RIZATRIPTAN BASE; To a solution of 200 g of 1-(4-aminophenyl)-methyl-1 ,2,4 triazole dihydrochloride in 2000 ml water was added 158 ml of concentrated hydrochloric acid and 180 g of 4-dimethyl-amino-butanal-dimethyl-acetal, and the mixture was maintained for 1-2 hours at 0-5 C. Another 158 ml of concentrated hydrochloric acid was added to the mixture and the mixture was heated to 70-75 C for 2 hours. The mixture was cooled to 25-30 C, quenched by adding 265 ml of 40% aqueous sodium hydroxide solution, and the product was extracted with 3000 ml of ethyl acetate three times. Combined organic layer was passed through 950 g of silica gel (60-120 mesh) packed in a glass column, and the clear solvent was collected and discarded. The silica gel was eluted with 8000 ml of isopropanol. Solvent was evaporated from the eluate to yield 101 g of the desired purified rizatriptan base having a dimer impurity content of 0.055 area-% as measured by HPLC.; EXAMPLE 5; Experiments were carried out using the general procedure of Example 1 , with different acid catalysts under aqueous and nonaqueous conditions, to determine influences on the yield and quality of the rizatriptan base product. As the dimer impurity was a major potential impurity formed during the process, quality of product was monitored with respect to the percentage of dimer impurity in the product. The results of the experiments are tabulated below:
40.29 - 50.28% sulfuric acid; In water; at 90 - 100℃;Product distribution / selectivity; EXAMPLE 5; Experiments were carried out using the general procedure of Example 1 , with different acid catalysts under aqueous and nonaqueous conditions, to determine influences on the yield and quality of the rizatriptan base product. As the dimer impurity was a major potential impurity formed during the process, quality of product was monitored with respect to the percentage of dimer impurity in the product. The results of the experiments are tabulated below:
  • 6
  • [ 179543-88-5 ]
  • [ 19718-92-4 ]
  • [ 1432472-65-5 ]
YieldReaction ConditionsOperation in experiment
68% With sulfuric acid; In water; for 2h;Reflux; [0489] Scheme 3: synthesis of 2-(5-methoxy-lH-indol-3-yl)-N,N-dimethylethanamine (KD19) and 2-(5-methoxy-lH-pyrrolo[3,2-b]pyridin-3-yl)-N,N-dimethylethanamine (KD20)[0490] A reported procedure was followed to prepare the compounds(i).
 

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