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[ CAS No. 949-69-9 ] {[proInfo.proName]}

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Chemical Structure| 949-69-9
Chemical Structure| 949-69-9
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Product Details of [ 949-69-9 ]

CAS No. :949-69-9 MDL No. :MFCD00277794
Formula : C12H16N2O Boiling Point : -
Linear Structure Formula :- InChI Key :VIMRHNNRKUWOIZ-UHFFFAOYSA-N
M.W : 204.27 Pubchem ID :70365
Synonyms :

Calculated chemistry of [ 949-69-9 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.42
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 64.55
TPSA : 35.83 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.5 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.26
Log Po/w (XLOGP3) : 1.47
Log Po/w (WLOGP) : 1.58
Log Po/w (MLOGP) : 1.59
Log Po/w (SILICOS-IT) : 2.25
Consensus Log Po/w : 1.83

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.2
Solubility : 1.3 mg/ml ; 0.00636 mol/l
Class : Soluble
Log S (Ali) : -1.83
Solubility : 3.03 mg/ml ; 0.0148 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.99
Solubility : 0.209 mg/ml ; 0.00102 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.72

Safety of [ 949-69-9 ]

Signal Word:Danger Class:4.1
Precautionary Statements:P201-P202-P280-P210-P240-P264-P270-P301+P310-P330-P370+P378-P403+P233-P405-P501 UN#:1325
Hazard Statements:H228-H312-H317-H318 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 949-69-9 ]

* 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.

  • Upstream synthesis route of [ 949-69-9 ]
  • Downstream synthetic route of [ 949-69-9 ]

[ 949-69-9 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 3612-20-2 ]
  • [ 949-69-9 ]
YieldReaction ConditionsOperation in experiment
100% With hydroxylamine hydrochloride; potassium carbonate In ethanol at 20℃; for 16 h; compound 1a (1.89 g, 10 mmol) was dissolved in 50 mL of absolute ethanol, and potassium carbonate (2.76 g, 20 mmol) and hydroxylamine hydrochloride (1.04 g, 15 mmol) were added successively and stirred at room temperature for 6 hours. After the mixture was concentrated, water was added. Then the mixture was extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated to give white solids 1b (2.04 g, yield 100percent), MS: 205.0 [M+H]+.
72% With hydroxylamine hydrochloride; sodium hydrogencarbonate In ethanol at 0 - 20℃; Step 1: Synthesis of l-benzylpiperidin-4-one oxime [141]To a clean and dried single necked round bottom flask was added hydroxyl amine hydrochloride (3.08 g, 0.04 mol), sodium bicarbonate (9.32 g, 0.1 1 mol), and ethanol (120 ml) at 0 °C. After 5 min compound [140] (7.0 g, 0.04 mol) was added dropwise at 0 °C. The reaction mixture was brought to RT in 2 h. TLC analysis showed complete consumption of starting material. The reaction was worked up by removing the ethanol by distillation followed by addition of water (50 ml), extracted into EtOAc (3 X 150 ml), combined the organic layer which were dried over sodium sulphate and concentrated to yield [141] as a white solid (5.5 g, 72 percent).ESIMS: 205 (M+ + 1)
72% With hydroxylamine hydrochloride; sodium hydrogencarbonate In ethanol at 0 - 20℃; for 2 h; Step l To a clean and dried single necked round bottom flask was added hydroxyl amine hydrochloride (3.08 g, 0.04 mol), sodium bicarbonate (9.32 g, 0. 1 1 mol), and ethanol (120 ml) at 0 °C. After 5 min compound [109] (7.0 g, 0.04 mol) was added dropwise at 0 °C. The reaction mixture was brought to RT in 2 h. TLC analysis showed complete consumption of starting material. ' The reaction was worked up by removing the ethanol by distillation followed by addition of water (50 ml), extracted into EtOAc (3 X 150: ml), combined the organic layer which were dried over sodium sulphate and concentrated to yield [110] as a white solid (5.5 g, 72 percent). ESIMS: 205 (M+ + 1 ) .
70.17% With hydroxylamine hydrochloride; potassium carbonate In ethanol; water at 0 - 20℃; 28.35 g ( 1 equiv., 0.15 mol) of 1-benzylpiperidin-4-one was dissolved in 60 mL of EtOH and then cooled to 0 °C using an ice bath. A solution containing 20.85 g (2 equiv., 0.30 mol) of hydroxylamine hydrochloride dissolved in 75 mL of H2O was prepared and then added dropwise to the reaction mixture followed by dropwise addition of a solution containing 20.7 g (1 equiv., 0.15 mol) of K2CO3 dissolved in 75 mL of H2O. The reaction mixture was then brought to room temperature and stirred overnight. The EtOH was then removed via rotary evaporation and the reaction mixture was then cooled in an ice bath to allow the product to crystallize out of solution. The product was filtered and washed several times with H2O and recrystallized in EtOH. Yield: 27.78 g (70.17percent).

Reference: [1] Patent: US2017/44187, 2017, A1, . Location in patent: Paragraph 0086; 0087
[2] European Journal of Medicinal Chemistry, 2010, vol. 45, # 7, p. 2827 - 2840
[3] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 14, p. 4085 - 4090
[4] Tetrahedron, 1995, vol. 51, # 17, p. 5143 - 5156
[5] Journal of Medicinal Chemistry, 2013, vol. 56, # 22, p. 9089 - 9099
[6] Patent: WO2012/101654, 2012, A2, . Location in patent: Page/Page column 73
[7] Patent: WO2014/16849, 2014, A2, . Location in patent: Page/Page column 124
[8] Patent: WO2016/29218, 2016, A1, . Location in patent: Page/Page column 12-13
[9] Patent: US5580872, 1996, A,
[10] Patent: US4481360, 1984, A,
[11] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 8, p. 2837 - 2842
  • 2
  • [ 3612-20-2 ]
  • [ 949-69-9 ]
YieldReaction ConditionsOperation in experiment
98% With sodium acetate In ethanol; water Stage A
1-benzyl-4-hydroxyiminopiperidine
18.9 g of 1-benzyl-4-oxopiperidine, 26.8 g of hydroxylamide hydrochloride, and 24.8 g of sodium acetate in 200 ml of ethanol are stirred for 8 hours.
The mixture is concentrated, taken up in 100 ml of water and rendered basic and the resulting precipitate is filtered off.
Yield: 98percent
Melting point: 125°-127° C.
Proton nuclear magnetic resonance spectrum (solvent CDCl3): 7.3 ppm, 5H, m; 3.55 ppm, 2H, s; 2.75 to 2.4 ppm, 6H, m; 2.35 ppm, 2H, m; 3 ppm, 1H exchangeable.
Reference: [1] Patent: US5189045, 1993, A,
  • 3
  • [ 20821-52-7 ]
  • [ 949-69-9 ]
Reference: [1] Journal of the Chemical Society, 1957, p. 3165,3171
  • 4
  • [ 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
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