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[ CAS No. 218451-34-4 ] {[proInfo.proName]}

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Chemical Structure| 218451-34-4
Chemical Structure| 218451-34-4
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Product Details of [ 218451-34-4 ]

CAS No. :218451-34-4 MDL No. :MFCD11227117
Formula : C17H21ClN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :GAAZJKMOIVSYQD-UHFFFAOYSA-N
M.W : 320.81 Pubchem ID :49760270
Synonyms :

Calculated chemistry of [ 218451-34-4 ]

Physicochemical Properties

Num. heavy atoms : 22
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.53
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 90.53
TPSA : 53.33 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.81 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.27
Log Po/w (XLOGP3) : 3.44
Log Po/w (WLOGP) : 3.75
Log Po/w (MLOGP) : 2.84
Log Po/w (SILICOS-IT) : 3.43
Consensus Log Po/w : 3.35

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.93
Solubility : 0.0373 mg/ml ; 0.000116 mol/l
Class : Soluble
Log S (Ali) : -4.24
Solubility : 0.0184 mg/ml ; 0.0000574 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.69
Solubility : 0.00654 mg/ml ; 0.0000204 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.3

Safety of [ 218451-34-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 218451-34-4 ]

* 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.

  • Upstream synthesis route of [ 218451-34-4 ]
  • Downstream synthetic route of [ 218451-34-4 ]

[ 218451-34-4 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 218451-34-4 ]
  • [ 91721-16-3 ]
YieldReaction ConditionsOperation in experiment
100% With trifluoroacetic acid In dichloromethane at 20℃; for 72 h; e) 4-(4-chlorophenyl)-4-cyanopiperidine. A solution containing 1-N-Boc-4-(4-chlorophenyl)-4-cyanopiperidine (1.32 g, 4.11 mmol), TFA (11 mL), and DCM (11 mL) was stirred at RT for 72 h, and then concentrated. The residue was treated with water and sat. aq. sodium bicarbonate (until basic), then extracted with DCM (3X). The DCM extracts were dried (Na2SO4), filtered, and concentrated to give the title compound (quant. ) as a colored oil. MS m/z 221 (M+H).
100%
Stage #1: With trifluoroacetic acid In dichloromethane at 20℃; for 0.5 h;
Stage #2: With sodium hydrogencarbonate In dichloromethane; water
A3. 4-(4-Chloro-phenyl)-piperidine-4-carbonitrile EPO <DP n="122"/>A solution of 4-(4-chloro-phenyl)-4-cyano-piperidine-l-carboxylic acid tert-butyl ester (15g, 47mmol), trifluoroacetic acid (30ml) and dichloromethane (30ml) was stirred at room temperature for 30 minutes. The reaction was then concentrated in vacuo and re- concentrated from dichloromethane (x3). The residue was then dissolved in dichloromethane, washed with saturated aqueous bicarbonate solution and concentrated again in vacuo. The desired compound was obtained as a white solid (11.4g, 100percent yield)
98% With hydrogenchloride In 1,4-dioxane; methanol at 20℃; for 20 h; To a solution of 4-(4-chlorophenyl)-4-cyanopiperidine-l-carboxylic acid tert-butyl ester (1.000 g, 3.12 mmol) in methanol (5 ml) at rt was added 4M HCl in dioxane (15 ml). After stirring for 20 h the solution was concentrated to give the deprotected amine as the hydrochloride salt (0.785 g, 98percent). LC-MS (LCT2) m/z 221 [M+Η+], Rt 2.84 min.
82% With trifluoroacetic acid In dichloromethane Step 3:
4-(4-Chloro-phenyl)-piperidine-4-carbonitrile
To a chilled solution of 4-(4-chloro-phenyl)-4-cyano-piperidine-1-carboxylic acid tert-butyl ester (315 mg, 1 mmol) in 5 ml dichloromethane was added 1 ml trifluoroacetic acid.
The reaction was stirred at 0° C. for 3 hours, then concentrated under vacuum.
The resulting oil was diluted with dichloromethane and washed twice with saturated aqueous sodium bicarbonate.
The aqueous washings were extracted three times with dichloromethane.
The combined organic layers were dried with magnesium sulfate and concentrated under vacuum to yield the title compound (180 mg, 82percent).
1H-NMR (CDCl3) δ: 1.9-2.1 (4H, m), 3.0-3.2 (4H, m), 7.3-7.5 (4H, m).
MS m/z: 221 (M+1).
82% With trifluoroacetic acid In dichloromethane at 0℃; for 3 h; Step 3
4-(4-Chloro-phenyl)-piperidine-4-carbonitrile
To a chilled solution of 4-(4-chloro-phenyl)-4-cyano-piperidine-1-carboxylic acid tert-butyl ester (315 mg, 1 mmol) in 5 ml dichloromethane was added 1 ml trifluoroacetic acid.
The reaction was stirred at 0° C. for 3 hours, then concentrated under vacuum.
The resulting oil was diluted with dichloromethane and washed twice with saturated aqueous sodium bicarbonate.
The aqueous washings were extracted three times with dichloromethane.
The combined organic layers were dried with magnesium sulfate and concentrated under vacuum to yield the title compound (180 mg, 82percent).
1H-NMR (CDCl3) δ: 1.9-2.1 (4H, m), 3.0-3.2 (4H, m), 7.3-7.5 (4H, m).
MS m/z: 221 (M+1)
73% With hydrogenchloride In methanol at 20℃; for 2 h; Cooling with ice Example 39A4-(4-chlorophenyl)piperidine-4-carbonitrileTo a solution of compound Example 39A2 (1.8 g, 5.6 mmol) in MeOH (5 mL) was added dropwise HCl/MeOH (20 mL) with ice-bath. After addition, the mixture was warmed to room temperature and stirred for 2 hours. The mixture was concentrated and the residue was dissolved in water (30 mL) and washed with ethyl acetate. The aqueous layers were basified to pH=9 with IN NaOH solution and then extracted with ethyl acetate (3 x 50 mL). The combined organics were washed with brine, dried over Na2S04, filtered, and concentrated to afford Example 39A (0.9 g, 73percent) as a white solid.

Reference: [1] Patent: WO2004/22539, 2004, A1, . Location in patent: Page 34
[2] Patent: WO2006/136829, 2006, A2, . Location in patent: Page/Page column 119-120
[3] Patent: WO2006/46024, 2006, A1, . Location in patent: Page/Page column 135
[4] Patent: US2005/70549, 2005, A1,
[5] Patent: US2016/31908, 2016, A1, . Location in patent: Paragraph 1207; 1208; 1209
[6] Patent: WO2013/10453, 2013, A1, . Location in patent: Page/Page column 126
[7] Patent: WO2006/51290, 2006, A2, . Location in patent: Page/Page column 123
  • 2
  • [ 118753-70-1 ]
  • [ 140-53-4 ]
  • [ 218451-34-4 ]
YieldReaction ConditionsOperation in experiment
71% With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 60℃; Inert atmosphere Step 1. To the solution of 2-(4-chlorophenyl)acetonitrile (20.1 g, 132.59 mmol, 1.00 equiv) and tert-butyl N,N-bis(2-chloroethyl)carbamate (35.4 g, 146.19 mmol, 1.10 equiv) in anhydrous DMF (200 mL) was added sodium hydride (27g, 60percent in mineral oil,666.73 mmol, 3.00 equiv) portionwise at 0°C under N2 over 2 hr. The resulting solution was stirred at 60°C for 1.5 hr, and then stirred overnight at room temperature. The reaction was quenched by the careful addition of 250 mL of sat. aq. NH4C1. The resulting solution was extracted with 3x200 mL of dichloromethane. The combined extracts were washed with 2x300 mL of brine, then dried over anhydrous sodium sulfate andconcentrated under vacuum. The residue was purified on a silica gel column with dichloromethane/petroleum ether (1:1). 30 g (71percent) of tert-butyl 4-(4-chlorophenyl)-4- cyanopiperidine-1-carboxylate was obtained as a yellow solid. TLC: Rf = 0.15; ethyl acetate/petroleum ether = 1/5.
71% With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 60℃; Inert atmosphere Sodium hydride (27 g, 60percent in mineral oil, 666.73 mmol) was added dropwise over 2 hours at 0 Was added portionwise to 2- (4-chlorophenyl) acetonitrile (20.1 g, 132.6 mmol)And tert-butyl N, N-bis (2-chloroethyl) carbamate (35.4 g, 146.2 mmol) in dry DMF (200 mL).The resulting solution was stirred for 1.5 h at 60 ° C and overnight at ambient temperature.The reaction was quenched by careful addition of saturated aqueous ammonium chloride (250 mL).The resulting solution was extracted with DCM (3 x 200 mL). The combined organic extracts were washed with brine (2 x 300 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified with a silica gel column with DCM / petroleum ether (1: 1).Appropriate fractions were combined and evaporated to give tert-butyl 4- (4-chlorophenyl) -4-cyanopiperidine-l-carboxylate (30 g, 71percent) as a yellow solid. TLC: Rf = 0.15; EtOAc / petroleum ether = 1/5.
70% With sodium hydride In N,N-dimethyl-formamide at 20 - 65℃; for 90 h; 4-Chlorophenylacetontrile was reacted with three equivalents of sodium hydride and one equivalent of N-tert-butyloxycarbonyl-bis-(2-chloroethyl)amine in DMF, initially at room temperature and then at 6O0C to give, after work up, the N- protected piperidine nitrile title compound. Sodium hydride (60percent dispersion in mineral oil, 2.9 g, 72.3 mmol) was added in small portions, over a period of 1 hour, to a solution of .pound.z,y-(2-chloro-ethyl)- carbamic acid tert-butyl ester (6.74 g, 28 mmol) and 4-chlorobenzyl cyanide (3.8 g, 25 mmol) in anhydrous dimethylformamide (25 ml). The reaction mixture was heated at 65 0C for 1 hour and then stirred at room temperature for 89 hours. After this period, the reaction mixture was poured into ice/water (60 ml) and extracted with ethyl acetate (2 x 100 ml). The combined organic layers were washed with water and brine, dried, filtered and concentrated. Flash column chromatography on silica, eluting with hexane/dichloromethane/ethyl acetate (8:1 :1), gave 4-(4- chlorophenyl)-4-cyano-piperidine-l-carboxylic acid tert-butyl ester (5.6 g, 17.5 mmol, 70percent) as a white solid. LC-MS (LCT) m/z 320 [M+], R, 7.71 min.
70% With sodium hydride In N,N-dimethyl-formamide at 20 - 65℃; for 91 h; EXAMPLE 14C-r4-(4-Chloro-phenyl)-1-(7H-pyrrolof2,3-dipyrimidin-4-yl)-piperidin-4-yl1-methylamine 14A. 4-(4-Chlorophenvl)-4-cvanopiperidin-1-carboxvlic acid ferf-butvl ester4-Chlorophenylacetontrile was reacted with three equivalents of sodium hydride and one equivalent of N-terf-butyloxycarbonyl-bis-(2-chloroethyl)amine in DMF, initially at room temperature and then at 6O0C to give, after work up, the N-protected piperidine nitrile title compound.; 42B. 4-(4-Chlorophenvπ-4-cvano-piperidine-1-carboxylic acid tert-butyl esterSodium hydride (60percent dispersion in mineral oil, 2.9 g, 72.3 mmol) was added in small portions, over a period of 1 hour, to a solution of ib/s-(2-chloro-ethyl)-carbamic acid tert- butyl ester (6.74 g, 28 mmol) and 4-chlorobenzyl cyanide (3.8 g, 25 mmol) in anhydrous dimethylformamide (25 ml). The reaction mixture was heated at 65 0C for 1 hour and then stirred at room temperature for 89 hours. After this period, the reaction mixture was poured into ice/water (60 ml) and extracted with ethyl acetate (2 x 100 ml). The combined organic <n="144"/>layers were washed with water and brine, dried, filtered and concentrated. Flash column chromatography on silica, eluting with hexane/dichloromethane/ethyl acetate (8:1:1), gave 4-(4-chlorophenyl)-4-cyano-piperidine-1-carboxylic acid ferf-butyl ester (5.6 g, 17.5 mmol, 70percent) as a white solid. LC-MS (LCT) m/z 320 [M +], R1 7.71 min.
54% With sodium hydride In DMF (N,N-dimethyl-formamide) at 20 - 65℃; for 74 h; f) 1-N-Boc-4- (4-chlorophenyl)-4-cyanopiperidine. A solution containing bis [(2-chloroethyl)-N-BOC amine (3.72 g, 15.38 MMOL), 4-chlorobenzyl cyanide (2.10 g, 13.88 mmol), and anhydrous DMF (15 mL) was stirred and NaH (60percent dispersion in mineral oil) (1.6 g, 40 mmol) was added in portions over 1 h. The mixture was heated at 60-65 °C. for 1 h, stirred at RT for 72h, then was poured into ice/water and extracted with EtOAc (2x). The organic extracts were washed (water and brine), dried, filtered, and concentrated. The residue was purified by chromatography (8: 1: 1 hexane/DCM/EtOAc) to give the title compound (2.4 g) (54 percent) as a yellow solid. MS m/z 221 (M-BOC).
54% With sodium hydride In N,N-dimethyl-formamide; mineral oil at 60℃; for 16 h; Step 2
4-(4-Chloro-phenyl)-4-cyano-piperidine-1-carboxylic acid tert-butyl ester
To 1.26 g (8.37 mmol) 4-chloro-benzylcyanide was added bis-(2-chloroethyl)-carbamic acid tert-butyl ester (2.02 g, 8.37 mmol) in 25 ml N, N-dimethylformamide.
The resulting mixture was stirred and cooled in an ice bath, then sodium hydride (60percent suspension in mineral oil) (1.1 g, 42 mmol) was added portionwise.
The reaction was brought to room temperature and then heated in an oil bath at 60° C. for 16 hours.
The reaction mixture was quenched by addition of ice water and the aqueous phase was extracted with ethyl acetate.
The combined organic layers were washed twice with water, once with brine, dried with magnesium sulfate and concentrated in vacuo.
The residual brown oil was purified by silica gel chromatography eluting with hexane-ethyl acetate (9:1) to give the title compound (1.44 g, 54percent).
1H-NMR (CDCl3) δ: 1.5 (9H, s), 1.8-2.0 (2H, m), 2.1 (2H, d), 3.2 (2H, t), 4.3 (2H, brs), 7.4 (4H, m).
MS m/z: 221 (M+1-100)
51% With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 60℃; for 17 h; General procedure: To a solution of 7 (1.66mmol) and substituted benzeneacetonitrile (1.66mmol) in anhydrous DMF (5mL) was added NaH (60percent dispersion in mineral oil, 8.4mmol) portion wise at 0°C over 1h. The reaction mixture was heated at 60°C for 16h. The reaction mixture was poured into ice-water (50mL) and extracted with ethyl acetate (3×50mL). The combined organic layers were washed with brine (2×50mL), dried over sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel chromatography eluting with ether/ethyl ether (15:1) to give 8a-8g.

Reference: [1] Patent: WO2015/32286, 2015, A1, . Location in patent: Page/Page column 310; 311
[2] Patent: CN107428750, 2017, A, . Location in patent: Paragraph 0548; 0551; 0552; 0553; 0554
[3] Journal of Medicinal Chemistry, 2008, vol. 51, # 7, p. 2147 - 2157
[4] Patent: WO2006/46024, 2006, A1, . Location in patent: Page/Page column 122; 146
[5] Patent: WO2007/125321, 2007, A2, . Location in patent: Page/Page column 120; 141-142
[6] Patent: US2005/70549, 2005, A1,
[7] Patent: WO2004/22539, 2004, A1, . Location in patent: Page 34
[8] Patent: US2016/31908, 2016, A1, . Location in patent: Paragraph 1204; 1205; 1206
[9] MedChemComm, 2018, vol. 9, # 8, p. 1340 - 1350
[10] European Journal of Medicinal Chemistry, 2017, vol. 138, p. 543 - 551
[11] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 21, p. 7213 - 7230
[12] Patent: US2005/176722, 2005, A1, . Location in patent: Page/Page column 13
[13] Patent: WO2004/20411, 2004, A1, . Location in patent: Page 19
  • 3
  • [ 623-03-0 ]
  • [ 118753-70-1 ]
  • [ 218451-34-4 ]
YieldReaction ConditionsOperation in experiment
41% With sodium hydride In N,N-dimethyl-formamide at 60℃; Cooling with ice; Inert atmosphere Example 39A2tert-butyl 4-(4-chlorophenyl)-4-cyanopiperidine- 1 -carboxylate To a mixture of Example 39A1 (3.5 g, 14.5 mmol) and 4-Chloro-benzonitrile (2.0 g, 13.2 mmol) in DMF (50 ml) was added NaH (2.1 g, 43.5 mmol) in portions with ice- bath under nitrogen atmosphere. After addition, the mixture was heated to 60 °C and stirred overnight. After cooling to room temperature, the mixture was poured into ice water (200 mL) and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2S04, filtered and concentrated. The residue was purified on silica column to afford Example 39A2 (1.8 g, 41percent) as a white solid.
Reference: [1] Patent: WO2013/10453, 2013, A1, . Location in patent: Page/Page column 126
  • 4
  • [ 24424-99-5 ]
  • [ 218451-34-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 21, p. 7213 - 7230
[2] Patent: WO2013/10453, 2013, A1,
[3] European Journal of Medicinal Chemistry, 2017, vol. 138, p. 543 - 551
[4] Patent: US2016/31908, 2016, A1,
[5] MedChemComm, 2018, vol. 9, # 8, p. 1340 - 1350
[6] Patent: WO2006/46024, 2006, A1,
[7] Patent: WO2007/125321, 2007, A2,
  • 5
  • [ 118753-70-1 ]
  • [ 218451-34-4 ]
Reference: [1] Patent: WO2006/51290, 2006, A2, . Location in patent: Page/Page column 120-121; 133
[2] Patent: WO2006/136829, 2006, A2, . Location in patent: Page/Page column 119
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