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[ CAS No. 187217-99-8 ]

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Chemical Structure| 187217-99-8
Chemical Structure| 187217-99-8
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CAS No. :187217-99-8 MDL No. :MFCD09040660
Formula : C7H13F3N2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :182.19 g/mol Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 187217-99-8 ]

  • Downstream synthetic route of [ 187217-99-8 ]

[ 187217-99-8 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 29051-44-3 ]
  • [ 187217-99-8 ]
  • [ 1033836-10-0 ]
YieldReaction ConditionsOperation in experiment
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethylacetamide (DMA); at 20℃; for 1h; To a 250 mL 3-necked flask containing 2-phenyl-5-pyridinecarboxylic acid (2.75 g, 13.8 mmol) in N,N-dimethylacetamide (DMA, 35 mL) was added N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDAC/EDC*HCl, 2.95 g, 15.2 mmol), 1-hydroxybenzotriazole (HOBt. 1.89 g, 13.8 mmol), 1-(2,2,2-trifluoroethyl)piperidin-4-amine (3.36 g, 15.2 mmol) and 4-methylmorpholine (NMM, 3.8 mL, 34.5 mmol). After stirring at room temperature for 1 hour, the reaction was diluted with water (200 mL) and the resulting solid collected by filtration. The solid was washed with H2O (3.x.100 mL), collected and dried in a vacuum oven (45° C.) overnight to give the desired product (4.24 g). LCMS (ES+) 4.30 min (TIC, 75percent; 1H NMR purity >95percent); 1H NMR (400 MHz, DMSO-d6) ppm 1.46-1.65 (m, 2 H) 1.77 (d, J=10.80 Hz, 2 H) 2.31-2.54 (m, 4 H) 2.90 (d, J=11.53 Hz, 2 H) 3.65-3.86 (m, 1 H) 7.36-7.56 (m, 3 H) 8.01 (d, J=8.24 Hz, 1 H) 8.09 (d, J=6.95 Hz, 2 H) 8.22 (d, J=8.42 Hz, 1 H) 8.38 (d, J=7.32 Hz, 1 H) 9.02 (s, 1 H); MS(ES+) 364 (M+1); HRMS (TOF, ES+) calculated for C19H20F3N3O+H+: 364.1637; observed 364.1611.
  • 2
  • [ 187217-99-8 ]
  • [ 505082-91-7 ]
  • [ 1033844-11-9 ]
YieldReaction ConditionsOperation in experiment
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl acetamide; at 20℃; for 1.0h; To a vial was added <strong>[505082-91-7]6-(2-fluorophenyl)nicotinic acid</strong> (100 mg, 0.46 mmol), 1-(2,2,2-trifluoroethyl)piperidin-4-amine (83.8 mg, 0.46 mmol), EDAC (97.1 mg, 0.51 mmol), HOBT (62.2 mg, 0.46 mmol), DMA (2 mL) and NMM (0.127 mL, 1.15 mmol). The reaction was stirred for 1 hour at room temperature and then diluted with EtOAc (0.2 mL) followed by H2O (4 mL). The resulting solids were washed in H2O and collected by filtration. 1 H NMR (400 MHz, DMSO-d6) ppm 9.11 (1 H, d, J=1.9 Hz), 8.52 (1 H, d, J=7.5 Hz), 8.28 (1 H, dd, J=8.3, 2.3 Hz), 7.94-8.05 (1 H, m), 7.90 (1 H, dd, J=8.4, 1.5 Hz), 7.50-7.58 (1 H, m), 3.72-3.89 (1 H, m), 3.19 (2 H, q, J=10.3 Hz), 2.95 (2 H, d, J=11.9 Hz), 2.40-2.48 (2 H, m) 1.82 (2 H, d, J=13.1 Hz), 1.52-1.67 (2 H, m).
  • 3
  • [ 187217-99-8 ]
  • [ 582325-22-2 ]
  • [ 1033836-12-2 ]
YieldReaction ConditionsOperation in experiment
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl acetamide; at 20℃; for 2h; 1-(2,2,2-Trifluoroethyl)piperidin-4-amine was synthesized as in steps a-c of Example 1. To a 250 mL round bottom flask containing <strong>[582325-22-2]6-(3-fluorophenyl)pyridine-3-carboxylic acid</strong> (see Example 3, Step A)(2.01 g, 9.25 mmol ) in DMA (35 mL) was added EDAC/EDC*HCl(1.95 g, 10.2 mmol), HOBt (1.38 g, 10.2 mmol), 1-(2,2,2-trifluoroethyl)piperidin-4-amine (1.85 g, 10.2 mmol) and NMM (2.23 mL, 20.4). After stirring at room temperature for 2 hours the reaction mixture was diluted with water (100 mL) and the resulting solid filtered and dried to give the desired product (2.96 g). LCMS (ES+) 4.55 min (TIC, 90%; 1H NMR purity >95%);1H NMR (400 MHz, DMSO-d6) ppm 1.60 (dq, J=11.84, 3.48 Hz, 2 H) 1.81 (d, J=10.62 Hz, 2 H) 2.44 (t, J=11.16 Hz, 2 H) 2.50 (br. s., 2 H) 2.94 (d, J=11.53 Hz, 2 H) 3.74-3.87 (m, 1 H) 7.32 (dt, J=8.37, 2.29 Hz, 1 H) 7.57 (q, 1 H) 7.96 (d, J=10.43 Hz, 1 H) 8.01 (d, J=7.69 Hz, 1 H) 8.14 (d, J=8.24 Hz, 1 H) 8.28 (dd, J=8.24, 2.20 Hz, 1 H) 8.49 (d, J=7.50 Hz, 1 H) 9.07 (d, J=1.83 Hz, 1 H); MS(ES+) 382 (M+1); HRMS (TOF, ES+) calculated for C19H19F4N3O+H+: 382.1542; observed 382.1548.
  • 4
  • [ 187217-99-8 ]
  • [ 887975-97-5 ]
  • [ 1033844-50-6 ]
YieldReaction ConditionsOperation in experiment
With 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; at 20.0℃; To a solution of <strong>[887975-97-5]6-(3-cyanophenyl)nicotinic acid</strong> (50 mg, 0.222 mmol) in dimethylformamide (1 mL) was added 1,11-carbonylbis(1H-imidazole) (36.3 mg, 0.224 mmol) and the reaction mixture stirred at room temperature for 1 hour. A solution of 1-(2,2,2-trifluoroethyl)piperidin-4-amine (49 mg, 0.269 mmol) in dimethylformamide (0.5 mL) was then added and the reaction stirred overnight at room temperature. Further 1,11-carbonylbis(1H-imidazole) (18 mg, 0.132 mmol) was added and the reaction stirred for 30 minutes and then further 1-(2,2,2-trifluoroethyl)piperidin-4-amine (25 mg, 0.134 mmol) in dimethylformamide (0.5 mL) was added and the solution stirred for one hour. The dimethylformamide was evaporated off and the residue partitioned between ethyl acetate (10 mL) and water (3 mL). The organic layer was separated, dried over anhydrous MgSO4, filtered and evaporated to a white solid. This was triturated with t-butyl methyl ether and the white solid was filtered off and dried to give 6-(3-cyanophenyl)-N-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]nicotinamide 53mg 1 H NMR (400 MHz, DMSO-d6) ppm 1.57-1.67 (m, 2H) 1.80-1.87 (m,2H) 2.43-2.54 (m, 2H) 2.93-2.99 (m, 2H) 3.20 (q, J=10.1 Hz, 2H) 3.83 (m , 1H) 7.76(t, J=8.2 Hz, 1H) 7.97 (m, 1H) 8.24 (m, 1H) 8.34 (dd, J=6.2, 2.4 Hz, 1H) 8.52 (m, 2H) 8.61 *m, 1H) 9.12 (m,1 H) LCMS 389 (M+1) ELSD 1.27 minutes.
  • 5
  • [ 81363-14-6 ]
  • [ 187217-99-8 ]
  • [ 1033844-86-8 ]
YieldReaction ConditionsOperation in experiment
With ammonia; hydrogen;palladium 10% on activated carbon; In methanol; under 2068.65 Torr; for 18h; A 25% aqueous solution of ammonia (170 mL), 10% Pd/C (7.4 g), and a solution of the above <strong>[81363-14-6]1-(2,2,2-trifluoroethyl)piperidin-4-one</strong> /butanol mixture (72.5 g, 0.344 mol, 86:14 weight ratio) in methanol (420 mL) were placed into a 2 L glass autoclave purged with argon. The reaction mixture was hydrogenated in a Parr apparatus at a hydrogen pressure of 40 psi for 18 h. The catalyst was removed by filtration. The filtrate was concentrated in vacuo to 150 mL. Potash (46 g) and ether (200 mL) were added, and the mixture was vigorously stirred for 20 min. The organic layer was separated, and the aqueous one was extracted with ether (100 mL). The combined organic layers were dried over anhydrous Na2SO4 and evaporated to afford a mixture (74.4 g) of 1-(2,2,2-trifluoroethyl)piperidin-4-amine and 1-(2,2,2-trifluoroethyl)-N-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]piperidin-4-amine in 72:28 weight ratio (contain butanol). This mixture was fractionated at 7-8 mmHg on a 15 cm Vigreaux column (a fraction with bp 75-95 C. was collected) to afford 1-(2,2,2-trifluoroethyl)piperidin-4-amine (38.5 g) as a colorless liquid.
  • 6
  • [ 81363-14-6 ]
  • [ 187217-99-8 ]
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