Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 333954-86-2 | MDL No. : | MFCD14155813 |
Formula : | C17H22N2O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ODHVBWQNZTWKCV-UHFFFAOYSA-N |
M.W : | 302.37 | Pubchem ID : | 23019443 |
Synonyms : |
|
Num. heavy atoms : | 22 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.53 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 87.32 |
TPSA : | 62.56 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.98 cm/s |
Log Po/w (iLOGP) : | 3.42 |
Log Po/w (XLOGP3) : | 3.05 |
Log Po/w (WLOGP) : | 2.96 |
Log Po/w (MLOGP) : | 1.78 |
Log Po/w (SILICOS-IT) : | 2.35 |
Consensus Log Po/w : | 2.71 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.51 |
Solubility : | 0.0939 mg/ml ; 0.00031 mol/l |
Class : | Soluble |
Log S (Ali) : | -4.03 |
Solubility : | 0.0282 mg/ml ; 0.0000933 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -3.6 |
Solubility : | 0.0751 mg/ml ; 0.000248 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.49 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | Stage #1: With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1 h; Stage #2: at 60℃; for 0.5 h; |
Step A: tert-Butyl-4-(4-cvanophenyloxy)- 1 -piperidinecarboxylate <n="102"/>To tert-butyl 4-hydroxy- 1 -piperidinecarboxylate (24.1 g, 100. 0 mmol) in dimethylformamide (250 mL) is added sodium hydride (60percent emulsion in mineral oil) (8.00 g, 200.0 mmol) and the mixture is stirred at rt for 1 h. 4-Fluorobenzonitrile (12.1 g, 100.0 mmol) is added, the mixture is heated to 60 0C for 30 minutes, diluted with ethyl acetate and the reaction is quenched by the addition of water. The organic phase is evaporated in vacuo and purified on silica gel to give the desired product (27.5 g, 91percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | Stage #1: With sodium hydride In DMF (N,N-dimethyl-formamide) at 50℃; for 0.75 h; Stage #2: at 50℃; for 2 h; |
Example 9 4- (1-Benzyl-piperidin-4-yloxy)-benzamide Step 1 4- (4-Cyano-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester Add a solution of N-Boc-4-hydroxypiperidine (3.0 g, 14.9 mmol) in DMF (5 mL) to a suspension of sodium hydride (894 mg, 22.4 mmol) in DMF (17 mL). Stir the reaction mixture while heating at 50°C for 45 min. Then add a solution of 4-fluoro- benzonitrile (2.16 g, 17.9 mmol) in DMF (5 mL). Stir and heat at 50°C for 2h. Let cool to room temperature and quench with water (0.5 mL). Evaporate DMF. Redissolved the resulting residue in EtOAc/hexanes (2/1,20 mL) and wash with water (3x15 mL). Dry the organic layer over magnesium sulfate, filter and concentrate. Purify by chromatography (EtOAc/hexanes 20percent and EtOAc/hexanes 10percent) to yield the title compound (2.32 g, 52percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55.8% | With potassium carbonate In N,N-dimethyl-formamide at 100℃; | Step (i): Preparation of 4-(4-Cyano phenoxy) piperidine-l-carboxylic acid tert-butyl esterA solution of 4-hydroxy benzonitrile (15 g, 0.126 moles), potassium carbonate (28.89 g, 0.208 moles) and 4-(Toluene-4-sulfonyloxy) piperidine-l-carboxylic acid tert-butyl ester (57.62 g, 0.162 moles) in dimethylformamide (150 mL) was stirred at 100 °C while monitoring the progress of the reaction by thin layer chromatography. After completion of reaction, the reaction mass was quenched on to water (400 mL) and extracted with ethyl acetate (3 x 300 mL). The resulting ethyl acetate layer was washed with brine solution, dried over sodium sulfate and concentrated under reduced pressure to obtain the crude residue, which was further purified by flash chromatography using (ethyl acetate: hexane,l :9) to afford the title compound 21.25 g (Yield: 55.8 percent). - NMR (δ ppm): 1.47 (9H, s), 1.74 - 1.80 (2H, m), 1.91 - 1.96 (2H, m) 3.33 - 3.40 (2H, m), 3.66 - 3.72 (2H, m), 4.53 - 4.57 (1H, m), 6.94 - 6.96 (2H, d, J = 8.78 Hz), 7.57 - 7.59 (2H, d, J = 8.76 Hz);Mass (m/z): 303.4 (M+H)+. |
55.8% | With potassium carbonate In N,N-dimethyl-formamide at 100℃; | Step (i): Preparation of 4-(4-Cyano phenoxy)piperidine-1-carboxylic acid tert-butyl ester A solution of 4-hydroxy benzonitrile (15 g, 0.126 moles), potassium carbonate (28.89 g, 0.208 moles) and 4-(Toluene-4-sulfonyloxy)piperidine-1-carboxylic acid tert-butyl ester (57.62 g, 0.162 moles) in dimethylformamide (150 mL) was stirred at 100° C. while monitoring the progress of the reaction by thin layer chromatography. After completion of reaction, the reaction mass was quenched on to water (400 mL) and extracted with ethyl acetate (3*300 mL). The resulting ethyl acetate layer was washed with brine solution, dried over sodium sulfate and concentrated under reduced pressure to obtain the crude residue, which was further purified by flash chromatography using (ethyl acetate:hexane, 1:9) to afford the title compound 21.25 g (Yield: 55.8percent). 1H-NMR (δ ppm): 1.47 (9H, s), 1.74-1.80 (2H, m), 1.91-1.96 (2H, m) 3.33-3.40 (2H, m), 3.66-3.72 (2H, m), 4.53-4.57 (1H, m), 6.94-6.96 (2H, d, J=8.78 Hz), 7.57-7.59 (2H, d, J=8.76 Hz); Mass (m/z): 303.4 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67.6% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 25℃; for 4 h; | Tert-butyl-4-hydroxypiperidine-1-carboxylate (4.5 g, 22.4 mmol)4-hydroxybenzonitrile (2.7 g, 22.7 mmol)And triphenylphosphine(8.8 g, 33.5 mmol) was dissolved in tetrahydrofuran (80 mL)Cooled to 0 ° C,Diethyl azodicarboxylate (5.8 g, 33.3 mmol) was added.25 ° C for 4 hours,LC-MS detection reaction is completed,Concentrated, ethyl acetate (150 mL) and water (50 mL) were added,The aqueous phase was extracted with ethyl acetate (50 mL)Combined organic phase,The residue was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 10: 1) to give the product (4.6 g, 67.6percent yield). |
[ 609781-33-1 ]
tert-Butyl 4-(4-carbamoylphenoxy)piperidine-1-carboxylate
Similarity: 0.80
[ 210962-44-0 ]
tert-Butyl 4-(4-(ethoxycarbonyl)phenoxy)piperidine-1-carboxylate
Similarity: 0.80
[ 138227-63-1 ]
tert-Butyl 4-(4-aminophenoxy)piperidine-1-carboxylate
Similarity: 0.78
[ 95798-23-5 ]
Benzyl 4-hydroxypiperidine-1-carboxylate
Similarity: 0.77
[ 648418-25-1 ]
Benzyl 4-hydroxyazepane-1-carboxylate
Similarity: 0.75
[ 609781-33-1 ]
tert-Butyl 4-(4-carbamoylphenoxy)piperidine-1-carboxylate
Similarity: 0.80
[ 210962-44-0 ]
tert-Butyl 4-(4-(ethoxycarbonyl)phenoxy)piperidine-1-carboxylate
Similarity: 0.80
[ 138227-63-1 ]
tert-Butyl 4-(4-aminophenoxy)piperidine-1-carboxylate
Similarity: 0.78
[ 1032903-63-1 ]
tert-Butyl 4-(4-amino-5-isopropoxy-2-methylphenyl)piperidine-1-carboxylate
Similarity: 0.74
[ 66605-58-1 ]
(S)-tert-Butyl (1-(4-(benzyloxy)phenyl)-3-hydroxypropan-2-yl)carbamate
Similarity: 0.73
[ 609781-33-1 ]
tert-Butyl 4-(4-carbamoylphenoxy)piperidine-1-carboxylate
Similarity: 0.80
[ 210962-44-0 ]
tert-Butyl 4-(4-(ethoxycarbonyl)phenoxy)piperidine-1-carboxylate
Similarity: 0.80
[ 952681-82-2 ]
2-(1'-(tert-Butoxycarbonyl)spiro[chroman-2,4'-piperidine]-4-yl)acetic acid
Similarity: 0.79
[ 138227-63-1 ]
tert-Butyl 4-(4-aminophenoxy)piperidine-1-carboxylate
Similarity: 0.78
[ 95798-23-5 ]
Benzyl 4-hydroxypiperidine-1-carboxylate
Similarity: 0.77
[ 161609-84-3 ]
Benzyl 4-cyanopiperidine-1-carboxylate
Similarity: 0.74
[ 849237-14-5 ]
1-Boc-4-(4-Cyanobenzyl)piperazine
Similarity: 0.72
[ 333986-52-0 ]
1-Boc-4-[(4-cyanophenyl)amino]-piperidine
Similarity: 0.70
[ 873551-20-3 ]
tert-Butyl 4-cyano-5,6-dihydropyridine-1(2H)-carboxylate
Similarity: 0.69
[ 609781-33-1 ]
tert-Butyl 4-(4-carbamoylphenoxy)piperidine-1-carboxylate
Similarity: 0.80
[ 210962-44-0 ]
tert-Butyl 4-(4-(ethoxycarbonyl)phenoxy)piperidine-1-carboxylate
Similarity: 0.80
[ 138227-63-1 ]
tert-Butyl 4-(4-aminophenoxy)piperidine-1-carboxylate
Similarity: 0.78
[ 95798-23-5 ]
Benzyl 4-hydroxypiperidine-1-carboxylate
Similarity: 0.77
[ 1032903-63-1 ]
tert-Butyl 4-(4-amino-5-isopropoxy-2-methylphenyl)piperidine-1-carboxylate
Similarity: 0.74
[ 609781-33-1 ]
tert-Butyl 4-(4-carbamoylphenoxy)piperidine-1-carboxylate
Similarity: 0.80
[ 210962-44-0 ]
tert-Butyl 4-(4-(ethoxycarbonyl)phenoxy)piperidine-1-carboxylate
Similarity: 0.80
[ 952681-82-2 ]
2-(1'-(tert-Butoxycarbonyl)spiro[chroman-2,4'-piperidine]-4-yl)acetic acid
Similarity: 0.79
[ 138227-63-1 ]
tert-Butyl 4-(4-aminophenoxy)piperidine-1-carboxylate
Similarity: 0.78
[ 95798-23-5 ]
Benzyl 4-hydroxypiperidine-1-carboxylate
Similarity: 0.77