[ CAS No. 174855-57-3 ] {[proInfo.proName]}

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Quality Control of [ 174855-57-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 174855-57-3 ]

SDS Specification

Alternatived Products of [ 174855-57-3 ]

Product Details of [ 174855-57-3 ]

CAS No. :	174855-57-3	MDL No. :	MFCD05864664
Formula :	C₁₆H₂₂N₂O₃	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	FGJACYJASSSXNJ-UHFFFAOYSA-N
M.W :	290.36	Pubchem ID :	6490990
Synonyms :

Calculated chemistry of [ 174855-57-3 ] Expand+

Physicochemical Properties

Num. heavy atoms :	21
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.5
Num. rotatable bonds :	5
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	89.03
TPSA :	49.85 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.53 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.98
Log Po/w (XLOGP3) :	2.17
Log Po/w (WLOGP) :	1.79
Log Po/w (MLOGP) :	1.53
Log Po/w (SILICOS-IT) :	1.88
Consensus Log Po/w :	2.07

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.89
Solubility :	0.375 mg/ml ; 0.00129 mol/l
Class :	Soluble
Log S (Ali) :	-2.85
Solubility :	0.41 mg/ml ; 0.00141 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.02
Solubility :	0.277 mg/ml ; 0.000953 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.31

Safety of [ 174855-57-3 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P280-P305+P351+P338	UN#:
Hazard Statements:	H317-H319	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 174855-57-3 ]

* 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 [ 174855-57-3 ]

[ 174855-57-3 ] Synthesis Path-Downstream 1~12

1
[ 33966-50-6 ]
[ 174855-57-3 ]
4-[2-(sec-butylamino-methyl)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 3793 - 3796

2
[ 5813-64-9 ]
[ 174855-57-3 ]
4-{2-[(2,2-dimethyl-propylamino)-methyl]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 3793 - 3796

3
[ 78-81-9 ]
[ 174855-57-3 ]
4-[2-(isobutylamino-methyl)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 3793 - 3796

4
[ 75-04-7 ]
[ 174855-57-3 ]
4-(2-ethylaminomethyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 3793 - 3796

5
[ 446-52-6 ]
[ 57260-71-6 ]
[ 174855-57-3 ]

Yield	Reaction Conditions	Operation in experiment
42.7%	With potassium carbonate; In dimethyl sulfoxide; at 130℃; for 4.0h;Inert atmosphere;	Put 2-fluorobenzaldehyde (4.0g, 32.2mmol),Piperazine-tert-butyl formate (6.6 g, 35.4 mmol) was added to DMSO (96 mL), followed by potassium carbonate (6.4 g, 64.4 mmol). The reaction was heated to 130 C. for 4 hours under nitrogen protection. The reaction was stopped and cooled to room temperature. The reaction solution was quenched with water (100 mL), extracted with ethyl acetate (60 mL × 3), and the organic phase was collected, washed with water and saturated brine in sequence, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained crude product was subjected to silica gel chromatography. Column (petroleum ether: ethyl acetate (V: V) = 10: 1) was further purified to give the title compound (light yellow solid, 4.0 g, 42.7%).
8.5 g	With potassium carbonate; In dimethyl sulfoxide; at 100℃; for 12.0h;	To a solution of 2-fluorobenzaldehyde (13.33 g, 107.38 mmol) and tert-butyl piperazine-1-carboxylate (30.0 g, 161.07 mmol) in DMSO (150 mL) was added K 2CO 3 (44.52 g, 322.15 mmol). The mixture was stirred at 100C for 12 hr. TLC indicated the reactant was consumed completely. The reaction mixture was cooled to room temperature and poured into H 2O (150 mL) and extracted with EA (150 mL 3), dried over Na 2SO 4, filtered and concentrated. The residue was purified by column chromatography (Silica gel, PE/EA=100/1 to 30/1). Tert-butyl 4- (2-formylphenyl) piperazine-1-carboxylate (8.5 g) was obtained as a yellow solid. 1H NMR (400MHz, CDCl 3) δ ppm: 1.50 (s, 9 H), 3.02 -3.08 (m, 4 H), 3.61 -3.66 (m, 4 H), 7.11 (d, J=8.2 Hz, 1H), 7.17 (t, J=7.5 Hz, 1H), 7.52 -7.58 (m, 1H), 7.83 (dd, J=7.7, 1.8 Hz, 1H), 10.36 (s, 1H).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 3793 - 3796
[2]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4417 - 4423
[3]Journal of Medicinal Chemistry,2004,vol. 47,p. 6821 - 6830
[4]Journal of Organic Chemistry,2005,vol. 70,p. 8924 - 8931
[5]Synthesis,2010,p. 4287 - 4299
[6]Patent: CN108299338,2018,A .Location in patent: Paragraph 0142; 0144; 0145; 0146; 0147
[7]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5605 - 5609
[8]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 4817 - 4822
[9]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 4599 - 4604
[10]Patent: WO2019/210828,2019,A1 .Location in patent: Paragraph 0347; 0348; 0349

6
[ 616-24-0 ]
[ 174855-57-3 ]
4-{2-[(1-ethyl-propylamino)-methyl]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 3793 - 3796

7
[ 174855-57-3 ]
[ 179250-28-3 ]

Yield	Reaction Conditions	Operation in experiment
89%	With sodium tetrahydroborate; In methanol; at 0 - 20℃; for 2.0h;	Dissolve tert-butyl 4- (2-formylphenyl) piperazine-1-carboxylate (4.0 g, 13.8 mmol) in methanol (69 mL),Sodium borohydride (0.87 g, 20.7 mmol) was added at 0 C. After the addition was completed, the reaction was carried out at room temperature for 2 hours. Stop reactionIt was quenched with water and extracted with dichloromethane. The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.The obtained crude product was further purified by a silica gel chromatography column (petroleum ether: ethyl acetate (V: V) = 5: 1) to obtain the title compound.(Light yellow solid, 3.6 g, 89%).
1.1 g (95%)	With hydrogenchloride; sodium tetrahydroborate; In methanol; ethyl acetate;	Step B: 1-t-Butoxycarbonyl-4-(2-hydroxymethylphenyl)-piperazine A solution of 1.15 g (3.96 mmol) of 1-t-butoxycarbonyl-4-(2-formyl-phenyl)-piperazine in 10 mL of MeOH was treated with 0.15 g (3.96 mmol) of NaBH4. After 2 h the reaction was quenched by adding 1.2N HCl and the mixture was extracted with EtOAc. The EtOAc solution was washed with water, brine and dried. The filtrate was concentrated to yield 1.1 g (95%) of 1-t-butoxycarbonyl-4-(2-hydroxymethyl-phenyl)-piperazine as a white foam which was used without purification. 1 H NMR (CDCl3) δ 1.24 (s, 9H), 2.92 (m, 4H), 3.59 (m, 4H), 4.84 (s, 2H), 7.0-7.4 (m, 4H).

Reference： [1]Patent: CN108299338,2018,A .Location in patent: Paragraph 0142; 0148; 0149; 0150; 0151
[2]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 3793 - 3796
[3]Patent: US5607936,1997,A
[4]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 4817 - 4822

8
[ 123-75-1 ]
[ 174855-57-3 ]
[ 444581-99-1 ]