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[ CAS No. 153749-89-4 ]

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Chemical Structure| 153749-89-4
Chemical Structure| 153749-89-4
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CAS No. :153749-89-4 MDL No. :MFCD01861221
Formula : C11H18N2O2 Boiling Point : 325.3°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :210.27 g/mol Pubchem ID :2756784
Synonyms :

Safety of [ 153749-89-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302-H317 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 153749-89-4 ]

  • Upstream synthesis route of [ 153749-89-4 ]
  • Downstream synthetic route of [ 153749-89-4 ]

[ 153749-89-4 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 388077-74-5 ]
  • [ 153749-89-4 ]
YieldReaction ConditionsOperation in experiment
97% With pyridine; oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane; acetonitrile at -5 - 20℃; Acetonitrile (220 mL) and DMF (3.82 mL, 49.4 mmol) were added to a 500 mL round bottom flask equipped with stir bar. Cooled the mixture down to-5°C and to it added oxalyl chloride (24.7 mL, 49.4 mmol, 2 M dichloromethane). The resulting mixture was stirred for 15 min. This was followed by addition of solution of 2-carbamoyl-piperidine-1- carboxylic acid tert-butyl ester (9.4 g, 41.2 mmol) in acetonitrile. (50 mL) and pyridine (8.3 mL, 103 mmol). Reaction mixture was left stirring at room temperature overnight. The reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate (300 mL). The organic phase was successively washed with water (300 mL) and brine (200 mL), dried (sodium sulfate), filtered and concentrated in vacuo to isolate the title compound (8.44 g, 97percent) as a yellow solid. 1H NMR (CDCIs), 8 (ppm): 5.23 (bs, 1H), 4.03 (bs, 1H), 2.93 (t, 1H), 1.75 (m, 5H), 1.46 (m, 10H).
97%
Stage #1: With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane; acetonitrile at -5℃; for 0.25 h;
Stage #2: With pyridine In dichloromethane; acetonitrile at 20℃;
Piperidine-1, 2-dicarboxylic acid-1-tert-butyl ester (12.8 g, 55.6 mmol) and THF (170 mL) were added to a 500 mL round bottom flask equipped with stir bar. The solution was cooled to-20°C and triethylamine (10.1 mL, 72.3 mmol) was added followed by ethyl [CHLOROFORMATE] (5.32 mL, 55.6 [MMOL).] The resulting white precipitate was left stirring at- [10°C] for 1 h. Aqueous ammonia (22.6 mL, 1168 mmol) was added to the above reaction mixture and the clear reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo and the isolated residue was dissolved in ethyl acetate (300 [ML).] The organic phase was successively washed with water (300 mL) and brine (200 mL), dried (sodium sulfate), filtered and concentrated in vacuo to isolate a clear gum. The gum was triturated with hexanes to isolate the title compound (9.4 g, [74percent)] as a white [SOLID. LH-NMR (CDC13), 6] (ppm): 6.03 (bs, 1H), 5.55 (bs, 1H), 4.77 (bs, 1H), 4.05 (bs, 1H), 2.81 (t, 1H), 2.27 (bs, 1H), 1.47 (m, 14H). Acetonitrile (220 mL) and DMF (3.82 mL, 49.4 mmol) were added to a 500 [ML] round bottom flask equipped with stir bar. Cooled the mixture down to-5°C and to it added oxalyl chloride (24.7 mL, 49.4 mmol, 2 M dichloromethane). The resulting mixture was stirred for 15 min. This was followed by addition of solution of 2-carbamoyl-piperidine-1- carboxylic acid tert-butyl ester (9.4 g, 41.2 mmol) in acetonitrile (50 [ML)] and pyridine (8.3 mL, 103 [MMOL).] Reaction mixture was left stirring at room temperature overnight. The reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate (300 mL). The organic phase was successively washed with water (300 [ML)] and brine (200 mL), dried (sodium sulfate), filtered and concentrated in vacuo to isolate the title compound (8.44 g, 97percent) as a yellow [SOLID. LH-NMR (CDC13), 6 (PPM)] : 5.23 (bs, 1H), 4.03 (bs, 1H), 2.93 (t, 1H), 1.75 (m, [5H),] 1.46 (m, 10H).
Reference: [1] Patent: WO2005/80386, 2005, A1, . Location in patent: Page/Page column 42-43
[2] Patent: WO2004/14902, 2004, A2, . Location in patent: Page 39-40
[3] Synthetic Communications, 2007, vol. 37, # 21, p. 3793 - 3799
  • 2
  • [ 75844-69-8 ]
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Reference: [1] Journal of the American Chemical Society, 2008, vol. 130, # 32, p. 10496 - 10497
  • 3
  • [ 7677-24-9 ]
  • [ 75844-69-8 ]
  • [ 153749-89-4 ]
Reference: [1] Organic and Biomolecular Chemistry, 2009, vol. 7, # 2, p. 351 - 356
[2] Tetrahedron Letters, 2008, vol. 49, # 34, p. 5098 - 5100
  • 4
  • [ 7677-24-9 ]
  • [ 123387-55-3 ]
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Reference: [1] Bulletin of the Chemical Society of Japan, 1993, vol. 66, # 11, p. 3456 - 3463
  • 5
  • [ 19158-51-1 ]
  • [ 75844-69-8 ]
  • [ 153749-89-4 ]
Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8051 - 8055
[2] Synthesis (Germany), 2013, vol. 45, # 7, p. 874 - 887
  • 6
  • [ 98303-20-9 ]
  • [ 172876-96-9 ]
  • [ 153749-89-4 ]
Reference: [1] Chemical Science, 2017, vol. 8, # 3, p. 1790 - 1800
[2] Chimia, 2017, vol. 71, # 4, p. 226 - 230
  • 7
  • [ 75844-69-8 ]
  • [ 172876-96-9 ]
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Reference: [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 11, p. 1971 - 1975
  • 8
  • [ 10442-39-4 ]
  • [ 75844-69-8 ]
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Reference: [1] Journal of the American Chemical Society, 2008, vol. 130, # 32, p. 10496 - 10497
  • 9
  • [ 42457-10-3 ]
  • [ 24424-99-5 ]
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Reference: [1] Organic Letters, 2004, vol. 6, # 16, p. 2745 - 2748
  • 10
  • [ 7677-24-9 ]
  • [ 119910-09-7 ]
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Reference: [1] Heterocycles, 1988, vol. 27, # 7, p. 1685 - 1696
[2] Heterocycles, 1988, vol. 27, # 7, p. 1685 - 1696
  • 11
  • [ 98303-20-9 ]
  • [ 153749-89-4 ]
Reference: [1] Synthetic Communications, 2007, vol. 37, # 21, p. 3793 - 3799
[2] Patent: WO2004/14902, 2004, A2,
  • 12
  • [ 110-89-4 ]
  • [ 24424-99-5 ]
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Reference: [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 11, p. 1971 - 1975
  • 13
  • [ 24424-99-5 ]
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Reference: [1] Patent: WO2004/14902, 2004, A2,
  • 14
  • [ 4043-87-2 ]
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Reference: [1] Patent: WO2004/14902, 2004, A2,
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