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Chemical Structure| 22795-97-7 Chemical Structure| 22795-97-7

Structure of 22795-97-7

Chemical Structure| 22795-97-7

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Product Details of [ 22795-97-7 ]

CAS No. :22795-97-7
Formula : C7H16N2
M.W : 128.22
SMILES Code : CCN1CCC[C@@H]1CN
MDL No. :MFCD00671482

Safety of [ 22795-97-7 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225-H302-H315-H318-H335
Precautionary Statements:P261-P280-P305+P351+P338
Class:3(8)
UN#:2924
Packing Group:

Application In Synthesis of [ 22795-97-7 ]

* 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 [ 22795-97-7 ]

[ 22795-97-7 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 33045-53-3 ]
  • [ 22795-97-7 ]
  • [ 23756-79-8 ]
  • 2
  • [ 71675-87-1 ]
  • [ 22795-97-7 ]
  • [ 108-23-6 ]
  • (R)-(+)-4-amino-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-2-methoxybenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Dissolve 10 g of Amimic acid and 4.96 g of triethylamine in 50 ml of acetone, cool down to 5 C., slowly add 5.6 g of isopropyl chloroformate, and then dropwise, incubate at agitation for 0.5 h, and slowly add dropwise Example 1 A 25 mL solution of 6.42 g of R-2-aminomethyl-N-ethylpyrrolidine in acetone was prepared, and the mixture was stirred at 0° C. for 0.5 h and then stirred at room temperature for 1 h. The mixture was vortexed, water was added and extracted with dichloromethane (25 ml x 3). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and evaporated to dryness to give a yellow-brown oil.
  • 3
  • [ 71675-87-1 ]
  • [ 22795-97-7 ]
  • (R)-(+)-4-amino-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-2-methoxybenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
7 g With 4-methyl-morpholine; chloroformic acid ethyl ester; In acetone; at -10 - 20℃;Inert atmosphere; 10 g of <strong>[71675-87-1]4-amino-5-(ethylsulfonyl)-2-methoxybenzoic acid</strong>, 100 mL of acetone and 5.3 mL of 4-methyl morpholine were placed in a flask equipped with a stir bar, a thermocouple and a nitrogen line. The solution was cooled to 0 C., and then 4.4 mL of ethyl chloroformate was added to the reactor. The mixture was agitated at -10 C. and then 5.42 g of (R)-(1-ethylpyrrolidin-2-yl)methanamine was added dropwise. The mixture was agitated at -10 C. for 1 hour then warmed to ambient. The reaction was concentrated and 100 mL of water and 100 mL of ethyl acetate were added. The mixture was agitated and the organic layer removed. 100 mL of ethyl acetate and 40 mL of 10 wt % aqueous potassium carbonate were then added. The mixture was agitated and the phases were allowed to separate and the aqueous layer was removed. The ethyl acetate layer was then washed with 50 mL of water two times. The organic layer was transferred to a flask with a mechanical stirrer, a thermocouple and distillation head. The organic layer was concentrated to dryness and 10 g of ethyl acetate was added. The mixture was stirred then cooled to -10 C. and agitated until a slurry formed. The mixture was warmed to 0 C. and stirred at 0 C. for 2 h. The slurry was then filtered, washed with ethyl acetate and dried at ambient temperature. 7 g of (R)-4-Amino-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-2-methoxybenzamide ethyl acetate solvate, having greater than 99% chiral purity, and greater than 99% chemical purity, was obtained. An NMR spectrum of the (R)-4-Amino-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-2-methoxybenzamide ethyl acetate solvate obtained in Example 4A is illustrated in , having the following characteristics: 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.11 (t, J=7.24 Hz, 3H) 1.23-1.27 (m, 3H), 1.25 (t, J=7.17 Hz, 0.91H) 1.55-1.77 (m, 3H) 1.82-1.92 (m, 1H), 2.04 (s, 0.93H), 2.14-2.27 (m, 2H) 2.58-2.64 (m, 1H) 2.84 (dd, J=12.13, 7.43 Hz, 1H) 3.07-3.28 (m, 4H) 3.69 (ddd, J=13.50, 7.24, 2.74 Hz, 1H) 3.93 (s, 3H) 4.11 (q, J=7.17 Hz, 0.64H) 5.52 (s, 2H) 6.21 (s, 1H) 7.26 (s, 1H) 8.04 (br d, J=5.09 Hz, 1H) 8.52 (s, 1H).
150 g of <strong>[71675-87-1]4-amino-5-(ethylsulfonyl)-2-methoxybenzoic acid</strong> and 2000 g of acetone were placed in a flask. The solution was cooled to -9 C., and 74.3 mL of ethyl chloroformate was added to the flask. Then 88.9 mL of 4-methyl morpholine was added over 1 hour. 81.4 g of (R)-(1-ethylpyrrolidin-2-yl)methanamine was added and the mixture stirred for 16 h. The reaction was then concentrated and 800 g of water and 300 g of ethyl acetate were added. The mixture was agitated and the organic layer removed, which contained the R-4-Amino-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-2-methoxybenzamide starting material. The solution containing the starting material was basified by the addition of aqueous 20 wt % potassium carbonate and 2.5 L of ethyl acetate was added. The aqueous layer was removed. The organic layer was washed twice with water and concentrated to dryness. Then 800 g of ethyl acetate was added and the mixture was concentrated. This was repeated once. The resulting oil was dissolved into 800 g of ethyl acetate and concentrated to 600 mL. The solution was stirred at 30 C. and a slurry formed. The resulting slurry was cooled to 20 C. and agitated. 600 g of methyl t-butyl ether was added and the mixture stirred. The slurry was then filtered, washed with 3:1 wt/wt methyl t-butyl ether:ethyl acetate and dried. 165 g of R-4-Amino-N-[(1-ethyl -2-pyrrolidinyi)methyl]-5-(ethylsulfonyl)-2-methoxybenzamide was obtained as a crystalline solid.
  • 4
  • [ 71675-87-1 ]
  • [ 22795-97-7 ]
  • (R)-(+)-4-amino-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-2-methoxybenzamide L-tartrate [ No CAS ]
 

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[ 22795-97-7 ]

Chemical Structure| N/A

A695016 [N/A]

(R)-(1-Ethylpyrrolidin-2-yl)methanamine dihydrochloride

Reason: Free-Salt