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Chemical Structure| 3202-33-3 Chemical Structure| 3202-33-3
Chemical Structure| 3202-33-3

4-phenoxypiperidine

CAS No.: 3202-33-3

4.5 *For Research Use Only !

Cat. No.: A157231 Purity: 95%

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Product Details of [ 3202-33-3 ]

CAS No. :3202-33-3
Formula : C11H15NO
M.W : 177.24
SMILES Code : C1CC(CCN1)OC1=CC=CC=C1
MDL No. :MFCD04114971
InChI Key :KBYPITRKIJKGMD-UHFFFAOYSA-N
Pubchem ID :18878

Safety of [ 3202-33-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H317-H319
Precautionary Statements:P280-P305+P351+P338

Calculated chemistry of [ 3202-33-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 13
Num. arom. heavy atoms 6
Fraction Csp3 0.45
Num. rotatable bonds 2
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 56.76
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

21.26 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.3
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

2.02
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

1.44
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

1.73
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

2.27
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.95

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-2.42
Solubility 0.672 mg/ml ; 0.00379 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-2.09
Solubility 1.43 mg/ml ; 0.00806 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-3.34
Solubility 0.0803 mg/ml ; 0.000453 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.95 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.27

Application In Synthesis of [ 3202-33-3 ]

* 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 [ 3202-33-3 ]

[ 3202-33-3 ] Synthesis Path-Downstream   1~30

  • 1
  • [ 3202-33-3 ]
  • [ 740744-74-5 ]
  • 6-hydroxy-2-(4-phenoxypiperidine-1-carbonyl)-1H-quinolin-4-one [ No CAS ]
  • 2
  • [ 3202-33-3 ]
  • [ 36603-49-3 ]
  • [ 1025887-31-3 ]
  • 3
  • [ 40047-23-2 ]
  • [ 3202-33-3 ]
  • C20H20N2O3 [ No CAS ]
  • 4
  • [ 944240-54-4 ]
  • [ 3202-33-3 ]
  • C19H22N4O4 [ No CAS ]
  • 5
  • [ 3202-33-3 ]
  • [ 681509-05-7 ]
  • 6
  • [ 3202-33-3 ]
  • 2-methyl-6-nitro-2-[4-(4-phenoxy-piperidin-1-yl)-phenoxymethyl]-2,3-dihydro-imidazo[2,1-<i>b</i>]oxazole [ No CAS ]
  • 8
  • [ 3202-33-3 ]
  • methanesulfonic acid 3-(4-phenoxy-piperidin-1-yl)-propyl ester [ No CAS ]
  • 11
  • [ 3202-33-3 ]
  • 2,3-dimethoxy-6-(4-phenoxy-piperidine-1-sulfonyl)-benzoyl chloride [ No CAS ]
  • 12
  • [ 3202-33-3 ]
  • 2,3-dimethoxy-6-(4-phenoxy-piperidine-1-sulfonyl)-benzoic acid [ No CAS ]
  • 13
  • [ 3202-33-3 ]
  • <i>N</i>-hydroxy-2,3-dimethoxy-6-(4-phenoxy-piperidine-1-sulfonyl)-benzamide [ No CAS ]
  • 14
  • [ 3202-33-3 ]
  • 2,3-dimethoxy-6-(4-phenoxy-piperidine-1-sulfonyl)-<i>N</i>-(tetrahydro-pyran-2-yloxy)-benzamide [ No CAS ]
  • 15
  • [ 3202-33-3 ]
  • 3-(4-Phenoxy-piperidin-1-yl)-propylamine [ No CAS ]
  • 16
  • [ 3202-33-3 ]
  • N-[3-(4-Phenoxy-piperidin-1-yl)-propyl]-2,2-diphenyl-acetamide [ No CAS ]
  • 17
  • [ 295790-41-9 ]
  • [ 3202-33-3 ]
  • C20H25FN2O3S [ No CAS ]
  • 18
  • [ 3202-33-3 ]
  • [ 6601-22-5 ]
  • [ 639855-29-1 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20℃; for 16h; 4-Phenoxypiperidine (0.15g) was added to a solution of the product from step (i) (0.2g), [N,] N-diisopropylethylamine (1. [47ML)] in tetrahydrofuran and stirred at room temperature for 16h. The solvent was evaporated under reduced pressure and the residue purified by chromatography on silica eluting with ether/isohexane (1: 2). Yield 0.3g white solid. The solid was dissolved in N, [N-DIMETHYLFORMAMIDE] [(20ML),] sodium cyanide [(0.] lg) added and heated at [90C] for 32h. The mixture was partitioned between ethyl acetate and water, the organic layer separated, washed with water, brine, dried (MgS04) and evaporated under reduced pressure. The residue was purified by RPHPLC 35-95% acetonitrile in aqueous [TRIFLUOROACETIC] acid. Yield 0.079g MS: APCI (+ve) 367 (+H) [1HNMR] : (DMSO-d6) 8 7.31-6. 91 (5H, [M),] 4.66 [(1H,] [M),] 4.11-4. 04 (2H, [M),] 3.70- 3.57 [(10H,] [M),] 2.00-1. 95 (2H, m), 1.63-1. 60 (2H, [M)]
  • 19
  • [ 749898-77-9 ]
  • [ 3202-33-3 ]
  • 1-[[5-chloro-6-(4-phenoxy-1-piperidinyl)-3-pyridinyl]carbonyl]pyrrolidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 100℃; for 6h; The product from example 2 step a) (0.24g) and 4-PHENOXYPIPERIDINE (0. 18G) in NMP (5ML) and Hunigs base (0. 5ML) were heated at 100 C FOR 6h. The mixture was cooled and partitioned between ether and water. The phases were separated and the ether phase was dried (NA2SO4) and concentrated in vacuo. The resultant gum was purified by reverse phase HPLC (Symmetry, 75-5% aqueous, ammonium acetate (0.2% aq. ) in acetonitrile) to yield a gum, which on treatment with ethereal HC1 gave the title compound as a pale yellow solid (0.15g). MS (APCI+) 386 [M+H] + 'H NMR 6 (DMSO) 8.39 (d, LH), 7.92 (d, LH), 7.29 (ddt, 2H), 7.00 (dd, 2H), 6.93 (dt, LH), 4.64 (quintet, LH), 3.69 (dd, 2H), 3.47 (dd, 4H), 3.26 (ddd, 2H), 2.12-2. 03 (m, 2H), 1.91- 1.70 (m, 6H)
  • 20
  • [ 3202-33-3 ]
  • [ 64614-47-7 ]
  • 1-[[6-(4-phenoxy-1-piperidinyl)-3-pyridinyl]carbonyl]pyrrolidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 140℃; for 16h; The product of example 1 step b) (0. LUG), <strong>[3202-33-3]4-phenoxypiperidine</strong> (O. LG) and Hunigs base (0. 2ML) in NMP (5ML)) were heated at 140 C for 16h. The resulting mixture was concentrated in vacuo and purified by reverse phase HPLC (Symmetry, gradient 75- 5% aqueous, ammonium acetate (0.2% aq. ) in acetonitrile) to give the title compound as a solid (70mg). MS (APCI+) 352 [M+H] + 1H NMR 6 (CDC13) 8. 42 (d, lH), 7.75 (dd, lH), 7.30 (t, 2H), 7.00-6. 91 (m, 3H), 6.66 (d, LH), 4.62-4. 58 (m, LH), 4.00-3. 90 (m, 2H), 3.70-3. 50 (d, 6H), 2.10-1. 80 (m, 8H)
  • 21
  • [ 3202-33-3 ]
  • [ 226996-38-9 ]
YieldReaction ConditionsOperation in experiment
75% EXAMPLE 16 1-(2-Amino-benzothiazol-6-yl)-2-(4-phenoxy-piperidin-1-yl)-ethane Operating as in example 15, but employing <strong>[3202-33-3]4-phenoxy-piperidine</strong> instead of 4-benzyl-piperidine, the title compound was obtained in 75% yield, m.p. 164-167 C.
  • 22
  • [ 4783-86-2 ]
  • [ 100-39-0 ]
  • [ 3202-33-3 ]
YieldReaction ConditionsOperation in experiment
Pd-C; In methanol; acetone; EXAMPLE 5 4-Phenoxy-1-[(4-fluorophenoxy)propyl]piperidine STR42 A mixture of 4-phenoxypyridine and benzylbromide in acetone was stirred overnight at room temperature. After removal of the solvent, the residue was dissolved in methanol, cooled to -20 C. and treated portionwise with sodium borohydride, and warmed to 0 C. After a standard workup and purification, the resulting tetrahydropyridine adduct was dissolved in methanol and hydrogenated using 20% Pd-C as a catalyst to provide 4-phenoxypiperidine.
  • 23
  • [ 3202-33-3 ]
  • [ 1129-78-8 ]
  • 4-Phenoxy-1-[(4-fluorophenoxy)propyl]piperidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetone; A mixture of <strong>[3202-33-3]4-phenoxypiperidine</strong> and 1-bromo-3-(4-fluorophenoxy)propane in acetone with excess potassium carbonate was heated at reflux for 12 hours to give the title compound.
  • 24
  • [ 3202-33-3 ]
  • [ 180157-22-6 ]
YieldReaction ConditionsOperation in experiment
In 4-(S)-oxiranylmethoxy-1H-indole; EXAMPLE 38 Preparation of (2S)-(-)-1-(4-indolyloxy)-3-(4-phenoxypiperidin-1-yl)-2-propanol ethanedioate The title compound was prepared in similar fashion from (S)-(+)-4-(oxiranylmethoxy)-1H-indole and <strong>[3202-33-3]4-(phenoxy)piperidine</strong>. The resulting free base was dissolved in ethyl acetate, and precipitated with one equivalent of oxalic acid in ethyl acetate in 69% overall yield. FDMS m/e=366 (M+ of free base).
In 4-(S)-oxiranylmethoxy-1H-indole; Example 38 Preparation of (2S)-(-)-1-(4-indolyloxy)-3-(4-phenoxypiperidin-1-yl)-2-propanol ethanedioate The title compound was prepared in similar fashion from (S)-(+)-4-(oxiranylmethoxy)-1H-indole and <strong>[3202-33-3]4-(phenoxy)piperidine</strong>. The resulting free base was dissolved in ethyl acetate, and precipitated with one equivalent of oxalic acid in ethyl acetate in 69% overall yield. FDMS m/e=366 (M+ of free base).
  • 25
  • [ 3202-33-3 ]
  • [ 94526-95-1 ]
  • No.37 [ No CAS ]
  • 26
  • [ 169949-40-0 ]
  • [ 3202-33-3 ]
  • C23H25F3N2O4S [ No CAS ]
  • 27
  • [ 3202-33-3 ]
  • [ 6523-63-3 ]
  • 5-oxo-5-[4-phenoxyapiperidin-1-yl]-2,2-diphenylpentanenitrile [ No CAS ]
  • 28
  • [ 3202-33-3 ]
  • [ 1374779-39-1 ]
  • [ 1374779-40-4 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 5 - 20℃; for 16h; Example 160: 2-(6-Chlorobenzo[b1thiophene-2-carboxarnido)-5-(<strong>[3202-33-3]4-phenoxypiperidine</strong>-1- carbonvDbenzoic acidMethod 8A solution of t-butyl 5-methoxycarbonyl-2-nitrobenzoate (1 eq.) in THF-water (3:1) was treated with LiOH (1.1 eq.) and stirred over night at room temperature. The organic solvent was evaporated under vacuum, a small amount of water was added to obtain solution and the pH was adjusted to 6-7. The aqueous mixture was extracted with ethyl acetate, the organic layer was dried and concentrated under vacuum to afford a residue which was dissolved in MeOH and hydrogenated for 20 h in the presence of 10% palladium on carbon. After filtration of the catalyst through a Celite pad, the filtrate was concentrated under vacuum to afford t-butyl 2-amino-5-carboxybenzoate in 80% yield. This compound was dissolved in THF, 6-chlorobenzo[b]thiophenecarbonyl chloride (1.1 eq.) was added and the reaction mixture was refluxed for 14 h, cooled and concentrated under vacuum. The obtained residue was dissolved in DMF, <strong>[3202-33-3]4-phenoxypiperidine</strong> (1.2 eq.), EDCI (1.5 eq.), HOBt (0.5 eq.) and DIEA (2.5 eq.) were added at 5-10C, and stirring was continued at room temperature for 16 h. The reaction mixture was diluted with water and the precipitated solid was collected by suction filtration and dried. The compound was dissolved in dichloromethane, treated with TFA and stirred for 1 h at room temperature. Concentration of reaction mixture under vacuum and trituration with diethyl ether afforded the title compound, mp > 200C, in 27% overall yield.1 H-NMR (400 MHz, DMSO-d6, 300K), delta ppm: 12.70 (br.s, 1 H), 8.61 (m, 1 H), 8.28 (m, 1 H), 8.12-8.08 (m, 3H), 7.73 (m, 1 H), 7.53 (m, 1 H), 7.55-7.51 (m, 2H), 6.99 (m, 2H), 6.92 (m, 1 H), 4.67 (m, 1 H), 4.20-3.30 (m, 4H), 1.98 (m, 2H), 1.56 (m, 2H).MS, m/z = 535.3 [MH]+
  • 29
  • [ 333985-70-9 ]
  • [ 3202-33-3 ]
  • [ 1374602-22-8 ]
  • 30
  • [ 3202-33-3 ]
  • [ 35019-96-6 ]
  • 4-phenoxy-N-[(1SR,2RS)-2-phenylcyclopropyl]piperidine-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% With N-ethyl-N,N-diisopropylamine; In toluene; at 20℃; for 12h; General procedure: To a solution of 4-Phenoxypiperidine (333 mg, 1.88 mmol), N,N?-diisopropylethylamine (320 mul, 1.88 mmol) in toluene (3 ml) was added trans-2-phenylcyclopropyl isocyanate (racemic) (300 mg, 1.88 mmol), and the mixture was stirred for 12 h at room temperature. The reaction mixture was then poured into water and extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2SO4 and filtrated. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (3) (309 mg, 49%) as a white solid.
 

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Technical Information

Categories

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[ 3202-33-3 ]

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