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[ CAS No. 55186-89-5 ]

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2D
Chemical Structure| 55186-89-5
Chemical Structure| 55186-89-5
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Product Details of [ 55186-89-5 ]

CAS No. :55186-89-5MDL No. :MFCD00225259
Formula : C12H16N2O Boiling Point : -
Linear Structure Formula :-InChI Key :-
M.W :204.27Pubchem ID :239726
Synonyms :

Computed Properties of [ 55186-89-5 ]

TPSA : 32.3 H-Bond Acceptor Count : 2
XLogP3 : 0.8 H-Bond Donor Count : 1
SP3 : 0.42 Rotatable Bond Count : 2

Safety of [ 55186-89-5 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P280-P305+P351+P338UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 55186-89-5 ]

  • Upstream synthesis route of [ 55186-89-5 ]
  • Downstream synthetic route of [ 55186-89-5 ]

[ 55186-89-5 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 3612-20-2 ]
  • [ 55186-89-5 ]
YieldReaction ConditionsOperation in experiment
47%
Stage #1: at 0 - 5℃; for 27 h;
Stage #2: With sodium hydroxide In water
[Referential Example 119]; 1-Benzylhexahydro-1H-1,4-diazepin-5-one ; [] Concentrated sulfuric acid (25 mL) was added to 1-benzyl-4-piperidone (10.14 g) in acetic acid (50 mL) at room temperature, and sodium azide (3.880 g) was added thereto at 0°C over a period of 2 hours, followed by stirring at 5°C for 25 hours. The reaction mixture was alkalinized through addition of aqueous sodium hydroxide, followed by partitioning by use of chloroform. The aqueous layer was extracted with chloroform. The organic layers were combined, and washed with saturated brine, and then dried over sodium sulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure, and then the residue was purified through silica gel column chromatography (chloroform - methanol), to thereby give the title compound as a solid (5.081 g, 47percent).1H-NMR(400MHz,CDCl3)δ: 2.50-2.70(6H,m), 3.20-3.35(2H,m), 3.60(2H,s), 6.07(1H,br), 7.20-7.40(5H,m). MS(ESI)m/z: 205(M+H)+.
Reference: [1] Patent: EP1591443, 2005, A1, . Location in patent: Page/Page column 72
[2] Tetrahedron Letters, 1991, vol. 32, # 22, p. 2469 - 2470
[3] Patent: WO2012/101654, 2012, A2,
[4] Patent: WO2014/16849, 2014, A2,
  • 2
  • [ 949-69-9 ]
  • [ 55186-89-5 ]
YieldReaction ConditionsOperation in experiment
30%
Stage #1: With benzenesulfonyl chloride; sodium hydroxide In water; acetone; acetonitrile at 0℃; Reflux
Stage #2: With sodium hydroxide In acetone at 20℃;
Step 2: Synthesis of l-benzyl-l,4-diazepan-5-one [142]To a clean and dried two necked round bottom flask [141] (2 g, 0.00976 mol) was dissolved in acetone (20 ml) and acetonitrile (20 ml). The reaction mixture was cooled to 0 °C, and then to it 15 percent aqueous NaOH ( 1.2 ml) was added drop wise, followed by the addition of benzene sulphonyl chloride (1.49 ml, 0.01 1 mol). The reaction mixture was refluxed overnight. TLC showed complete consumption of SM. The reaction mixture was diluted with acetone, and passed through celite and concentrated. Saturated NaHC03 (50 ml) was added to the solid followed by extraction with EtOAc (3 X 150 ml), removal of the solvent under reduced pressure. The residue was purified by column chromatograph on silica gel with MeOH:DCM (1percent) as an eluent to afford [142] as a white solid (600 mg, 30 percent).ESIMS: 205 (M+ + 1)
30% With benzenesulfonyl chloride; sodium hydroxide In water; acetone; acetonitrile at 0℃; Reflux Step 2 To a clean and dried two necked round bottom flask [110] (2 g, 9.76 mmol) was dissolved in acetone (20 ml) and acetonitrile (20 ml). The reaction mixture was cooled to 0 (>C, and then to it 15 percent aqueous NaOH ( 1.2 ml) was added drop wise, followed by the addition of benzene sulphonyl chloride ( 1.49 ml, 1 1 mmol). The reaction mixture was refluxed overnight. TLC showed complete consumption of SM. The reaction mixture was diluted with acetone, and passed through celite and concentrated. Saturated NaHCOj (50 ml) was added to the solid followed by extraction with EtOAc (3 X 150 ml), removal of the solvent under reduced pressure. The residue was purified by column chromatography on silica gel with MeOH: DCM ( 1 ) as an eluent to afford [111] as a white solid (600 mg, 30 ). , ESIMS: 205 (M+ + 1 )
Reference: [1] Journal of Organic Chemistry, 1999, vol. 64, # 16, p. 5832 - 5835
[2] Patent: WO2012/101654, 2012, A2, . Location in patent: Page/Page column 73
[3] Patent: WO2014/16849, 2014, A2, . Location in patent: Page/Page column 124
  • 3
  • [ 55186-89-5 ]
  • [ 190900-21-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 23, p. 5907 - 5911
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