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[ CAS No. 428-38-6 ] {[proInfo.proName]}

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Chemical Structure| 428-38-6
Chemical Structure| 428-38-6
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Product Details of [ 428-38-6 ]

CAS No. :428-38-6 MDL No. :MFCD08705803
Formula : C13H17N Boiling Point : -
Linear Structure Formula :- InChI Key :ZBYFQSPEUIVDTF-UHFFFAOYSA-N
M.W : 187.28 Pubchem ID :15637616
Synonyms :

Calculated chemistry of [ 428-38-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.54
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 62.78
TPSA : 12.03 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.58 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.38
Log Po/w (XLOGP3) : 2.62
Log Po/w (WLOGP) : 1.87
Log Po/w (MLOGP) : 2.94
Log Po/w (SILICOS-IT) : 3.4
Consensus Log Po/w : 2.65

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.97
Solubility : 0.201 mg/ml ; 0.00107 mol/l
Class : Soluble
Log S (Ali) : -2.52
Solubility : 0.562 mg/ml ; 0.003 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.38
Solubility : 0.00784 mg/ml ; 0.0000419 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.04

Safety of [ 428-38-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 428-38-6 ]

* 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 [ 428-38-6 ]

[ 428-38-6 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 428-38-6 ]
  • [ 2279-15-4 ]
  • [ 185525-58-0 ]
  • 2
  • [ 428-38-6 ]
  • [ 5453-80-5 ]
  • 1'-((1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-ylmethyl)-2,3-dihydrospiro[indene-1,4'-piperidine] [ No CAS ]
YieldReaction ConditionsOperation in experiment
The starting Spiroindane 3i (45 mg, 0.2 mmol) was suspended in DCE (1 mL) and treated with (1S,2S,4S)-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde (25 mg, 0.2 mmol) in DCE, followed by the addition of NaBH(OAc)3 (63 mg, 0.3 mmol). The reaction was allowed to stir at room temperature for 1 h and was then quenched with MeOH (0.5 mL) and allowed to stir for another 30 min (until gas evolution stopped). The crude reaction mixture was filtered, then purified by HPLC (10-99% CH3CN/0.05% TFA gradient) to yield 1'-((1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-ylmethyl)-<strong>[428-38-6]2,3-dihydrospiro[indene-1,4'-piperidine]</strong> (compound no. 312). LC/MS m/z 294.4 [M+H]+, tR 2.33 min (RP-C18, 10-99% CH3CN/0.05% TFA); 1H NMR (400 MHz, DMSO-d6) δ 9.33 (br s, 1H), 7.25-7.17 (m, 3H), 7.13 (d, J=6.9 Hz, 1H), 6.27-6.26 (m, 1H), 6.06-6.04 (m, 1H), 3.56-3.40 (m, 3H), 3.11-3.03 (m, 2H), 2.98-2.78 (m, 6H), 2.09-1.98 (m, 5H), 1.67 (d, J=13.9 Hz, 2H), 1.36 (t, J=8.0 Hz, 1H), 1.29 (d, J=8.2 Hz, 1H), 0.70-0.66 (m, 1H).
  • 3
  • [ 428-38-6 ]
  • [ 845552-91-2 ]
  • 5-chloro-3-(2,3-dihydro-1'H-spiro[indene-1,4'-piperidin]-1'-ylmethyl)-3,4-dihydroisoquinolin-1(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
37.5% With sodium tris(acetoxy)borohydride; In tetrahydrofuran; at 20℃; for 72h; Example 29 5-CHLORO-3-(2, 3-DIHYDRO-1 H-SPIRO [INDENE-1, 4 -PIPERIDIN]-1 -YLMETHYL)-3, 4- dihydroisoquinolin-1 (2H)-one To a stirred suspension OF 5-CHLORO-L-OXO-1, 2,3, 4-tetrahydroisoquinoline-3-carboxylic acid (500 mg, 2.22 mmol) in THF (10 mL) was added borane-methyl sulfide complex (0.53 ML, 5.55 mmol) at 0 C. After 40 h stirring at room temperature, the reaction mixture was diluted with water (20 mL) and 2N HC1 (20 mL) and extracted with ethyl acetate (200 mL). The extract was washed with brine (40 ML), dried (NA2S04), filtered, and concentrated to give 336.4 mg of colorless gum. This was purified by silica gel column chromatography (CH2CL2/METHANOL : 20/1) to afford 193.5 mg (41.2 %) of alcohol derivative as a white solid. To a stirred solution of this solid (190 mg, 0.90 mmol) and triethylamine (0. 38 mL, 2.7 mmol) in DMSO (2.5 mL) was added sulfur trioxide pyridine complex (430 mg, 2.7 mmol) in DMSO (2.5 mL) at room temperature. After 1 h stirring, the reaction mixture was poured into ice water (100 mL) and extracted with ethyl acetate (100 ML). The extract was washed with aqueous 10 % citric acid solution (20 mL) and water (20 mL), dried (Na2S04), filtered, and concentrated to give 160 mg of aldehyde derivative. To a stirred suspension of this aldehyde derivative (160 mg) and 2,3-dihydrospiro [indene-1, 4'- piperidine] (70 mg, 0.37 mmol) in THF (5 mL) was added sodium triacetoxyborohydride (157 mg, 0.74 mmol) at room temperature. After 72 h stirring, the reaction mixture was diluted with water (10 mL), basified with saturated aqueous solution of NAHCO3, and extracted with CH2C12 (80 mL x 2). The extracts combined were dried (NA2S04), filtered, and concentrated to give 178 mg of yellow solid, which was purified by silica gel column chromatography (HEXANE/ETHYL acetate: 2/1) to afford 52. 8 mg (37.5 %) of title compound as a white solid. 1H NMR (300MHZ, CDC13) 8 8. 04 (1H, d, J = 7. 7 HZ), 7.52 (1H, d, J = 8. 1 Hz), 7.31 (1H, dd, J = 7.7, 8.0 Hz), 7.25-7. 16 (4H, m), 6.84 (1H, br. s), 3.94-3. 82 (1H, m), 3.22 (1H, dd, J = 3.7, 15.9 Hz), 2.90-2. 74 (4H, m), 2.66-2. 42 (4H, m), 2.17-1. 83 (5H, M), 1.60-1. 50 (2H, m). This solid was converted to citric acid salt similar to that described in Example 1. MS (ESI positive) M/Z : 381. 0 (M+H) +. IR (KBr) : 3400, 1719,1607, 1493,1450, 1383,1190, 959,754 CM Anal. Calcd for C23H25CLN2O-C6H807-2H2O : C, 57.19 ; H, 6.12 ; N, 4.60. Found: C, 57.36 ; H, 5.74 ; N, 4.35.
  • 4
  • [ 428-38-6 ]
  • [ 1663-39-4 ]
  • [ 574741-18-7 ]
YieldReaction ConditionsOperation in experiment
66% With triethylamine; In tetrahydrofuran; at 70℃; for 24h; tert-Butyl 3-(2,3-dihydro-1'H-spiro[indene-1,4'-piperidin]-1'-yl)propanoate A solution of 2, 3-dihydrospiro [indene-1, 4'-piperidine] (3.0 g, 13 mmol), tert- butyl acrylate (3.1 g, 24 mmol) and triethylamine (4.5 mL, 32 mmol) in tetrahydrofuran (60 mL) was stirred at 70 C under nitrogen atmosphere for 1 day. The organic layer was washed with saturated sodium bicarbonate aqueous solution (100 mL). The aqueous layer was extracted with ethyl acetate (150 mL x 2). The combined organic layers were washed with brine (50 mL), dried over sodium sulfate, and evaporated. The residue was purified by column chromatography on silica gel eluting with hexane/acetone (4/1) to afford 2.8 g (66%) of the title compound as a yellow oil: 'H-NMR (CDC13) 8 7.19-7. 12 (4H, m), 2.92-2. 85 (4H, m), 2.74-2. 69 (2H, m), 2.50- 2.45 (2H, m), 2.26-2. 17 (2H, m), 2.02-1. 87 (4H, m), 1.76-1. 67 (1H, m), 1.56-1. 52 (1H, m), 1.46 (9H, s).
  • 5
  • [ 428-38-6 ]
  • [ 638-45-9 ]
  • [ 137730-65-5 ]
YieldReaction ConditionsOperation in experiment
52% With potassium carbonate; In N,N-dimethyl-formamide; petrol; EXAMPLE 6 1'Hexylspiro[indane-1,4'-piperidine] In the same way as that described in Example 1, step 5, the title compound was synthesised using spiro[indane-1,4'-piperidine] (0.4 g, 2.2 mmol), DMF (15 ml), potassium carbonate (0.33 g, 2.4 mmol) and iodohexane (0.62 g, 2.9 mmol). The crude residue was chromatographed in 1:1 petrol:ether to give 1'-hexylspiro[indane-1,4'-piperidine] (314 mg, 52%) as a pale yellow oil. The hydrochloride salt of the title amine (300 mg, 1.1 mmol) was prepared using ethereal hydrogen chloride, to give 1'-hexylspiro[indane-1,4'-piperidine]hydrochloride (177 mg, 52%) as white crystals, after recrystallisation from ethyl acetate/ethanol. m.p. 283-287 C. N.M.R. (D2 O) δ 0.89 (3H, t, J=7 Hz), 1.35 (6H, m), 1.79 (4H, m), 2.13 (4H, m), 298 (2H, t, J=7 Hz), 3.17 (4H, m), 3.60 (2H, m) 7.31 (4H, m).
  • 6
  • [ 428-38-6 ]
  • [ 542-69-8 ]
  • [ 137730-64-4 ]
YieldReaction ConditionsOperation in experiment
53% With potassium carbonate; In methanol; dichloromethane; N,N-dimethyl-formamide; EXAMPLE 2 1'-n-Butylxpiro[indane-1,4'-piperidine] In the same way as that described in Example 1, step 5, the title compound was prepared using spiro[indane-1,4'-piperidine] (77 mg, 0.41 mmol), DMF (10 ml), potassium carbonate (68 mg, 0.49 mmol), and n-butyl iodide (0.05 ml, 0.45 mmol). The crude residue was chromatographed using 5:95 methanol: dichloromethane, to give 1'-n-butylspiro[indane-1,4'-piperidine] (53 mg, 53%) as a beige solid.
  • 7
  • [ 428-38-6 ]
  • [ 58001-94-8 ]
  • 1'-((1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-ylmethyl)-2,3-dihydrospiro[indene-1,4'-piperidine] [ No CAS ]
YieldReaction ConditionsOperation in experiment
The starting Spiroindane 3a (45 mg, 0.2 mmol) was suspended in DCE (1 mL) and treated with (lS,2S,4S)-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde (25 mg, 0.2 mmol) in DCE, followed by the addition of NaBH(OAc)3 (63 mg, 0.3 mmol). The reaction was allowed to stir at room temperature for 1 h and was then quenched with MeOH (0.5 mL) and allowed to stir for another 30 min (until gas evolution stopped). The crude reaction mixture was filtered, then purified by HPLC (10-99% CH3CN/0.05% TFA gradient) to yield compound no. 312. LC/MS m/z 294.4 [M+H]+, retention time 2.33 min (RP-Cig, 10-99% CH3CN/0.05% TFA); .H NMR (400 MHz, DMSO-d6) 8 9.33 (br s, 1H), 7.25-7.17 (m, 3H), 7.13 (d, J= 6.9 Hz, 1H), 6.27-6.26 (m, 1H), 6.06-6.04 (m, 1H), 3.56-3.40 (m, 3H), 3.11-3.03 (m, 2H), 2.98-2.78 (m, 6H), 2.09-1.98 (m, 5H), 1.67 (d, J= 13.9 Hz, 2H), 1.36 (t, J= 8.0 Hz, 1H), 1.29 (d, J= 8.2 Hz, 1H), 0.70-0.66 (m, 1H).
  • 8
  • [ 137419-24-0 ]
  • [ 428-38-6 ]
YieldReaction ConditionsOperation in experiment
With hydrogen;palladium 10% on activated carbon; In ethanol; for 2h; N-Boc spiro[lH-indene-l,4'-piperidine] (700 mg, 2.45 mmol) is added to ethanol (50 ml) in a Parr-shaker and hydrogenated over Pd/C (10%) for 2 h. The resulting reaction mixture is filtered through Celite and concentrated to dryness. The crude product is used without further purification for the next step.
  • 9
  • [ 428-38-6 ]
  • [ 2131-55-7 ]
  • [ 915104-46-0 ]
YieldReaction ConditionsOperation in experiment
87% With triethylamine; In dichloromethane; at 20℃; for 18h; Preparation 8: N-(4-Chlorophenyl)-2,3-dihydro-1'H-spiro[indene-1,4'-piperidine]-1'-carbothioamide. 4-Chlorophenyl isothiocyanate (683 mg, 4 mmol) was added dropwise to a solution of 2,3- dihydrospiro[indene-1,4'-piperidine] (900 mg, 4 mmol), [J. Med. Chem. 1992, 35, 2033] and triethylamine (0.67 ml, 4.83 mmol) in dichloromethane (20 ml), and the mixture was then stirred at room temperature for 18 hours. After which time it was partitioned between dichloromethane (200 ml) and an aqueous solution of 0.88 ammonia (100 ml). The aqueous layer was separated and extracted with dichloromethane (2 x 100 ml) and the combined organic solution was dried over magnesium sulfate and concentrated in vacuo to give a white foam. The foam was triturated with diethyl ether and the residue was dried under vacuum for 18 hours to afford the title compound as a solid in 87% yield, 1.25 g. 1HNMR(400MHz, CDCI3) δ: 1.68(m, 2H), 1.98(m, 2H), 2.12(m, 2H), 2.95(m, 2H), 3.30(t, 2H), 4.60(d, 2H), 7.09-7.35(m, 8H); LRMS ESI m/z 355 [M-H]+
  • 10
  • [ 428-38-6 ]
  • [ 71831-21-5 ]
  • [ 1292291-10-1 ]
YieldReaction ConditionsOperation in experiment
98% With caesium carbonate; In N,N-dimethyl-formamide; at 20℃; Preparation 55[4-(Spiro[indane-1,4'-piperidine]-1'-ylmethyl)phenyl]methanolTo a stirred solution of 2,3-dihydrospiro[indene-1,4'-piperidine] (0.4 g, 1.78 mmol) in DMF (12 mL) is added Cs2CO3 (1.4 g, 4.4 mmol) and <strong>[71831-21-5][4-(bromomethyl)phenyl]methanol</strong> (0.36 g, 1.78 mmol) and the reaction mixture is stirred overnight at room temperature. The reaction mixture is poured into cold water and extracted with EtOAc (3.x.50 mL). The combined organic layer is washed with brine solution, dried over Na2SO4, and concentrated under vacuum. The crude material is purified by silica gel chromatography (gradient DCM/MeOH 8/2) to give the title compound (0.6 g, 98percent). ESI/MS m/z 308.40 (M+H)+.
  • 11
  • [ 428-38-6 ]
  • [ 1292291-01-0 ]
  • [ 1292291-70-3 ]
YieldReaction ConditionsOperation in experiment
93.7% With caesium carbonate; In acetonitrile; at 20℃; Preparation 110Ethyl (3S)-3-[4-[[4-(spiro[indane-1,4'-piperidine]-1'-ylmethyl)phenyl]methoxy]phenyl]hex-4-ynoate To a solution of <strong>[428-38-6]2,3-dihydrospiro[indene-1,4'-piperidine]</strong> (0.37 g, 1.68 mmol) in acetonitrile (20.0 mL), is added Cs2CO3 (1.37 g, 4.21 mmol at room temperature, followed by the addition of 3-[4-(4-bromomethyl-benzyloxy)-phenyl]-hex-4-ynoic acid ethyl ester (0.70 g, 1.68 mmol). The reaction mixture is stirred overnight at room temperature. The reaction mixture is filtered through diatomaceous earth and the filtrate is evaporated. The crude product is purified by silica gel column chromatography (gradient 3% methanol in DCM) to give the title compound as colorless gel, (0.82 g, 93.7%). ESI/MS 522.2 (M+H)+.
  • 12
  • [ 428-38-6 ]
  • C15H18BrNO5 [ No CAS ]
  • C28H33BrN2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 24h;Inert atmosphere; General procedure: A mixture of 4-(4-fluoro-2-methylphenyl)piperidine 1 (386.5mg, 2.00mmol) that was prepared according to the reported method [6], compound 2 (554.6mg, 2.00mmol), water soluble carbodiimide, that is, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSCI) (766.8mg, 4.00mmol), hydroxybenzotriazole (HOBT) (540.5mg, 4.00mmol), and dry Et3N (836μL, 6.00mmol) in dry CH2Cl2 (16.0mL) was stirred at room temperature under N2 for 24h [7]. The reaction solution was poured into H2O (30mL), and the resulting mixture was extracted with CH2Cl2 (30mL×2). The combined extracts were dried over anhydrous MgSO4, and concentrated in vacuo. The residue was purified by column chromatography (silica gel, hexane/AcOEt=3:1) to afford 833.5mg of the title product 3 in 92% yield as a colorless oil.
  • 13
  • [ 428-38-6 ]
  • 2-[1-(4-oxo-3-[2-(trimethylsilyl)ethoxy]methyl}-3,4-dihydropyrido[3,4-d]pyrimidin-8-yl)-1H-pyrazol-4-yl]ethyl methanesulfonate [ No CAS ]
  • 8-(4-(2-(2,3-dihydrospiro[indene-1,4'-piperidin]-1'-yl)ethyl)-1H-pyrazol-1-yl)-3-((2-(trimethylsilyl)ethoxy)methyl)pyrido[3,4-d]pyrimidin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% With triethylamine; In N,N-dimethyl-formamide; at 50℃; for 15h;Inert atmosphere; General procedure: Triethylamine (2 equiv.) was added to a solution of freshly made (from compound 10) mesylate intermediate (1 equiv.) and amine (1.2 equiv.) in anhydrous DMF under N2. The reaction mixture was heated at 50C for 15h and monitored by LCMS. When the reaction had reached completion, the reaction mixture was diluted in H2O and extracted three times with EtOAc. The combined organic layers were washed with saturated LiCl solution, saturated brine solution, dried over MgSO4 and concentrated in vacuo to give the crude material which was purified by Biotage column chromatography (see individual compounds for details of the eluent used).
  • 14
  • [ 428-38-6 ]
  • C20H28N4O5SSi [ No CAS ]
  • C32H41N5O2Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
45.7% With triethylamine; In N,N-dimethyl-formamide; at 50℃; for 15h;Inert atmosphere; Triethylamine (13 mg, 0.13 mmol) was added to a solution of mesylate 38 (Hatch, S. B. et al,Epigenetics & Chromatin 2017, 10:9, DOI 10.1186/s13072-017-0116-6; 60 mg, 0.13 mmol,freshly made from alcohol precursor) and <strong>[428-38-6]2,3-dihydrospiro[indene-1,4'-piperidine]</strong> (29 mg,0.155 mmol) in anhydrous DMF (1 mL, 0.1 M) under N2. The reaction mixture was heated at50 C for 15 h and monitored by LCMS. When the reaction had gone to completion, thereaction mixture was diluted in H2O (5 mL) and extracted three times with EtOAc (3 × 5mL). The combined organic layers were washed with saturated sodium bicarbonate solution,dried over MgSO4, and concentrated in vacuo to give the crude material which was purifiedby flash silica chromatography eluting with 3% 7 N ammonia in methanol in CH2Cl2 yieldingthe title compound as a yellow oil (33 mg, 45.7%).
  • 15
  • [ 428-38-6 ]
  • [ 5292-43-3 ]
  • tert-butyl 2-(2,3-dihydrospiro[indene-1,4'-piperidin]-1'-yl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 20℃; for 2h; To a mixture of <strong>[428-38-6]2,3-dihydrospiro[indene-1,4'-piperidine]</strong> (Int 10a) (100 mg, 0.55 mmol) and tert-butyl 2-bromoacetate (129 mg, 0.66 mmol) in DCM (5 mL) was added TEA (139 mg, 1.38 mmol) and the mixture was stirred at rt for 2 h. Water (20 mL) was added and the mixture was extracted with DCM (20 mL). The combined organic layers were washed with water (30 mL) and brine (30 mL), dried over anhydrous Na2S04, filtered and concentrated to dryness to give the title compound as a white solid.
  • 16
  • [ 428-38-6 ]
  • [ 5445-17-0 ]
  • methyl 2-(2,3-dihydrospiro[indene-1,4'-piperidin]-1'-yl)propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 20℃; for 2h; To a mixture of <strong>[428-38-6]2,3-dihydrospiro[indene-1,4'-piperidine]</strong> (Int 10a) (100 mg, 0.55 mmol) and methyl 2-bromopropanoate (1 10 mg, 0.66 mmol) in DCM (5 mL) was added TEA (139 mg, 1.38 mmol) and the mixture was stirred at rt for 2 h. Water (20 mL) was added and the mixture was extracted with DCM (20 mL). The combined organic layers were washed with water (30 mL) and brine (30 mL), dried over anhydrous Na2S04 and concentrated to dryness to give the title compound as a white solid.
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