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[ CAS No. 875798-79-1 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 875798-79-1
Chemical Structure| 875798-79-1
Structure of 875798-79-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 875798-79-1 ]

CAS No. :875798-79-1 MDL No. :MFCD05861561
Formula : C16H24N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :SWUANUQBXJNXGP-UHFFFAOYSA-N
M.W : 276.37 Pubchem ID :44607626
Synonyms :

Calculated chemistry of [ 875798-79-1 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.56
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 85.48
TPSA : 55.56 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.09 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.02
Log Po/w (XLOGP3) : 2.67
Log Po/w (WLOGP) : 3.01
Log Po/w (MLOGP) : 2.45
Log Po/w (SILICOS-IT) : 2.06
Consensus Log Po/w : 2.64

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.19
Solubility : 0.177 mg/ml ; 0.00064 mol/l
Class : Soluble
Log S (Ali) : -3.49
Solubility : 0.0897 mg/ml ; 0.000325 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.43
Solubility : 0.103 mg/ml ; 0.000372 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.7

Safety of [ 875798-79-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 875798-79-1 ]

* 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 [ 875798-79-1 ]

[ 875798-79-1 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 138229-59-1 ]
  • [ 875798-79-1 ]
  • [ 1038915-99-9 ]
YieldReaction ConditionsOperation in experiment
85% With sodium hydrogencarbonate; acetic acid; at 40℃; for 2h; Take Niraparib intermediate 2 (0.4 mol) 89.6 g,Was added to 100 ml of methanol solution,Fully mixed,Then, 116.5 g (0.4 mol)Tert-butyl-3- (4-amino) phenylpiperidine-1-carboxylate,Half a drop of acetic acid as a catalyst,18 g (0.2 mol) of sodium bicarbonate,Heated to 40 reflux 2h,Cooled to room temperature to be precipitated after the crystal precipitation,Washed twice with ethanol and dried over anhydrous magnesium sulfate to give 169 g (0.34 mol) of Niraparib intermediate 3,The yield was 85%.
  • 2
  • [ 875798-79-1 ]
  • [ 1171197-20-8 ]
  • [ 1263284-59-8 ]
YieldReaction ConditionsOperation in experiment
With Chiralpak AD In ethanol; n-heptane Resolution of racemate; 150.a Example 150 3,4-Dichloro-N-((R)-4-piperidin-3-yl-phenyl)-benzamide hydrochloride(a) (R)-tert-Butyl 3 -(4-aminophenyl)piperidine-l -carboxylate & (S)-tert-Butyl 3-(4- aminophenyDpiperidine- 1 -carboxylate The enantiomers of (RS)-tert-butyl 3-(4-aminophenyl)piperidine-l -carboxylate (6.00 g, CAS 875798-79-1) were separated using chiral HPLC (column: Chiralpak AD, 5 x 50 cm; eluent: 10 % ethanol/heptane; pressure: 15 bar; flow rate: 35 ml/min) affording: (+)-(R)-tert-Butyl 3-(4-aminophenyl)piperidine- 1 -carboxylate (2.72 g, white solid)Retention time = 62 min (-)-(Sytert-Butyl 3-(4-aminophenyl)piperidine- 1 -carboxylate (2.65 g, white solid)Retention time = 88 min
With Chiralpak AD In ethanol; n-heptane Resolution of racemate; 150.a The enantiomers of (RS)-tert-butyl 3-(4-aminophenyl)piperidine-1-carboxylate (6.00 g, CAS 875798-79-1) were separated using chiral HPLC (column: Chiralpak AD, 5×50 cm; eluent: 10% ethanol/heptane; pressure: 15 bar; flow rate: 35 ml/min) affording:(+)-(R)-tert-Butyl 3-(4-aminophenyl)piperidine-1-carboxylate (2.72 g, white solid) Retention time=62 min (-)-(S)-tert-Butyl 3-(4-aminophenyl)piperidine-1-carboxylate (2.65 g, white solid) Retention time=88 min
With Chiralpak AD In ethanol; n-heptane Resolution of racemate; Large scale reaction;
  • 3
  • [ 34619-03-9 ]
  • [ 19733-56-3 ]
  • [ 875798-79-1 ]
  • 4
  • [ 19509-09-2 ]
  • [ 875798-79-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: acetic acid; sulfuric acid; nitric acid / 58 °C 2: triethylamine / dichloromethane / 2 h / 20 °C 3: tin(ll) chloride / water; N,N-dimethyl-formamide / 20 °C
  • 5
  • [ 875798-79-1 ]
  • [ 1171197-20-8 ]
YieldReaction ConditionsOperation in experiment
91.3% Stage #1: 3-(4-aminophenyl)piperidine-1-carboxylic acid tert-butyl ester With copper(l) iodide; (R)-1,1'-binaphthyl-2,2'-phosphoric acid In water; N,N-dimethyl-formamide at 50 - 75℃; for 2h; Stage #2: With hydrogenchloride; sodium hydroxide In water 1 A process for the preparation of tert-butyl (3S) -3- (4-aminophenyl) piperidine-1-carboxylate comprising the steps of 1) 27.6 g (100 mmol) of tert-butyl 3- (4-aminophenyl) piperidine-1-carboxylate, 38.3 g (110 mmol) of (R) - (-) - binaphthol phosphate, (20 mmol) were added to 150 ml of a mixed solvent consisting of DMF and water in a volume ratio of 5: 1. The mixture was then heated to 75 ° C. for 1 hour. After the reaction was continued, the mixture was stirred and allowed to cool to 50 ° C. Incubated for 1 hour, and then naturally cooled to room temperature, and filtered to obtain a solid compound A.2) hydrolyzing the solid compound A obtained in step 1) in 50 ml of 10% hydrochloric acid solution, adding sodium hydroxide after the completion of the hydrolysis reaction, adjusting the pH value to 10, extracting with ethyl acetate, concentrating, recrystallizing petroleum ether, vacuum The yield of tert-butyl (3S) -3- (4-aminophenyl) piperidine-1-carboxylate was 12.6 g, yield 91.3%, HPLC purity 99.91% by area normalization method, ee value 99.57% HPLC (Column: Chiralpak AD, 5 × 50 cm; eluent: 10% ethanol / heptane; pressure: 15 bar; flow rate: 35 ml / min).
  • 6
  • [ 19733-56-3 ]
  • [ 875798-79-1 ]
  • 7
  • [ 24424-99-5 ]
  • [ 19733-56-3 ]
  • [ 875798-79-1 ]
YieldReaction ConditionsOperation in experiment
2.67 g With sodium hydroxide; In methanol; water; at 0 - 20℃; A mixture of 4-(piperidin-3-yl) aniline (Compound 16) (2.0 g) in methanol (10 mL) and water (5 mL) in a reactor was cooled to 0-5C. NaOH (1.81 g) and Boc anhydride (2.59 g) was slowly charged with stirring to the reaction mixture. The reaction mass was stirred at 5-10C and then allowed to warm up to 20C until HPLC/TLC analysis indicated completion of reaction. The product was filtered, washed with water (6 mL) and methanol (2 mL) mixture. The solid was dried under vacuum at 50-55C to afford the titled compound (Yield: 2.67 g; HPLC Purity: > 95.0%).
  • 8
  • [ 875798-79-1 ]
  • [ 2743-38-6 ]
  • tert-butyl 3-(4-aminophenyl) piperidine-1-carboxylate dibenzoyl-L-tartaric acid salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
2.67 g With sodium hydroxide; In methanol; ethyl acetate; at 0 - 20℃; To a mixture of tert-butyl 3-(4-aminophenyl) piperidine-l- carboxylate (Compound 20) (0.5 g) in ethyl acetate (3.8 mL) and methanol (0.2 mL) in a reactor, <strong>[2743-38-6]dibenzoyl-L-tartaric acid</strong> (0.65 g) was added at 20-25C and followed by stirring for 5-6 h at 20-25C. The solid obtained was filtered, washed with MTBE (2 mL) and dried under vacuum at 50-55C to afford the titled compound (Yield: 0.18 g; Chiral Purity: >80% of Desired S-isomer).
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