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CAS No. : | 3939-01-3 | MDL No. : | MFCD00012799 |
Formula : | C14H18ClNO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BRADBAOVPACOQQ-UHFFFAOYSA-N |
M.W : | 283.75 | Pubchem ID : | 107479 |
Synonyms : |
|
Num. heavy atoms : | 19 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.43 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 78.2 |
TPSA : | 46.61 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.51 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 2.14 |
Log Po/w (WLOGP) : | 1.52 |
Log Po/w (MLOGP) : | 1.44 |
Log Po/w (SILICOS-IT) : | 2.04 |
Consensus Log Po/w : | 1.43 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.92 |
Solubility : | 0.343 mg/ml ; 0.00121 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.75 |
Solubility : | 0.504 mg/ml ; 0.00178 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.27 |
Solubility : | 0.153 mg/ml ; 0.000541 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.25 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
97.8% | With hydrogenchloride; potassium <i>tert</i>-butylate In toluene | Step A: 4-Oxo-1-(phenylmethyl)-3-piperidinecarboxylic acid methyl ester, hydrochloride . A solution of 1-benzyl-4-piperidone (56.5 kg, 1.0 eq.) in toluene (189 L) was prepared at 15°C to 25°C. A second reactor was charged with toluene (659 L), potassium tert-butoxide (71.9 kg, 2.25 eq.) and dimethyl carbonate (51.5 kg, 2.0 eq.) at 15°C to 25°C. The resulting slurry was warmed to a temperature of 80°C to 90°C. The solution of 1-benzyl-4-piperidone in toluene was added slowly to the slurry over 60 to 90 minutes. After an additional 90 minutes, the reaction mixture was cooled to below 15°C. The completed reaction was quenched with acetic acid (38.5 kg, 2.25 eq.) and water (367 L). The two phase mixture was separated. The organic layer was filtered to remove solids. The organic filtrate was concentrated by distillation under reduced pressure to a volume of approximately 150 L. Toluene (799 L) was added to the concentrated mixture. Addition of hydrogen chloride (gas, 11.0 kg, 1.05 eq.) afforded the hydrochloride salt as a precipitate. The slurry was stirred at 10°C to 15°C for 30 minutes. The solids were isolated by filtration, washed with approximately hexanes (130 L), and dried using vacuum to give 79.4 kg of 4-oxo-1-(phenylmethyl)-3-piperidinecarboxylic acid methyl ester, hydrochloride (97.8percent yield). Analysis calculated for C14H17NO3*HCl: C 59.3; H 6.39; N 4.94; found: C 59.7 H, 6.65 N, 4.85. |
97.8% | With hydrogenchloride; potassium <i>tert</i>-butylate In toluene | Step A: 4-Oxo-1-(phenylmethyl)-3-piperidinecarboxylic acid methyl ester, hydrochloride. A solution of 1-benzyl-4-piperidone (56.5 kg, 1.0 eq.) in toluene (189 L) was prepared at 15° C. to 25° C. A second reactor was charged with toluene (659 L), potassium tert-butoxide (71.9 kg, 2.25 eq.) and dimethyl carbonate (51.5 kg, 2.0 eq.) at 15° C. to 25° C. The resulting slurry was warmed to a temperature of 80° C. to 90° C. The solution of 1-benzyl-4-piperidone in toluene was added slowly to the slurry over 60 to 90 minutes. After an additional 90 minutes, the reaction mixture was cooled to below 15° C. The completed reaction was quenched with acetic acid (38.5 kg, 2.25 eq.) and water (367 L). The two phase mixture was separated. The organic layer was filtered to remove solids. The organic filtrate was concentrated by distillation under reduced pressure to a volume of approximately 150 L. Toluene (799 L) was added to the concentrated mixture. Addition of hydrogen chloride (gas, 11.0 kg, 1.05 eq.) afforded the hydrochloride salt as a precipitate. The slurry was stirred at 10° C. to 15° C. for 30 minutes. The solids were isolated by filtration, washed with approximately hexanes (130 L), and dried using vacuum to give 79.4 kg of 4-oxo-1-(phenylmethyl)-3-piperidinecarboxylic acid methyl ester, hydrochloride (97.8percent yield). Analysis calculated for C14H17NO3.HCl: C 59.3; H 6.39; N 4.94; found: C 59.7 H, 6.65 N, 4.85. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With hydrogen; triethylamine In ethanol for 24 h; | A suspension of L-BENZYL-4-OXOPIPERIDINE-3-CARBOXYLIC acid methyl ester hydrochloride (5.00 g, 17.6 mmol), triethylamine (2.45 mL, 17.6 mmol) and Boc20 (4.20 g, 20.0 mmol) in ETOH (30 mL) was purged with N2. PD/C (10percent, 600 mg) was added and the suspension purged with H2. The reaction mixture was stirred under an H2-ATMOSPHERE for 24 h and then filtered through Celite. The filtrate was evaporated under reduced pressure. Purification of the residue by FC (EtOAc/heptane 1 : 4 O 2: 3) yielded the title compound (4.02 g, 89percent). RF = 0.60 (EtOAc/heptane 1: 1). LC-MS: R, = 1.09 min, ES+ = 202.03 |
89% | With hydrogen; triethylamine In ethanol for 24 h; | A suspension of [1-BENZYL-4-OXOPIPERIDINE-3-CARBOXYLIC] acid methyl ester hydrochloride (5.00 g, 17.6 mmol), triethylamine (2.45 mL, 17.6 mmol) and Boc20 (4.20 g, 20.0 mmol) in [ETOH] (30 mL) was purged with [N2. PD/C] (10percent, 600 mg) was added and the suspension purged with H2. The reaction mixture was stirred under an H2-atmosphere for 24 h and then filtered through Celite. The filtrate was evaporated under reduced pressure. Purification of the residue by FC [(ETOAC/HEPTANE] 1: [4--2] : 3) yielded the title compound (4.02 g, [89percent).] Rf = 0.60 (EtOAc/heptane 1: 1). LC-MS: Rt = 1.09 min, ES+ = 202.03. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With sodium methylate In methanol for 18 h; Reflux | 7-Benzyl-4-(2-methylbenzyl)-1,2,6,7,8,9-hexahydroimidazo [1,2-a] pyrido [3,4-e] pyrimidin-5(4H)-one (2) (0104) A mixture of methyl 1-benzyl-4-oxopiperidine-3-carboxylate hydrochloride, 8, (568 mg, 2.0 mmol) and 7 (795 mg, 4.2 mmol) was treated with a solution of sodium methoxide in MeOH (0.5 M, 3.0 mL, 1.5 mmol). The mixture was stirred at a gentle reflux overnight. After 18 h, the reaction was cooled to room temperature, diluted with CH2Cl2 (50 mL), washed with brine (20 mL), dried over Na2SO4, filtered, and concentrated in vacuo. Purification by silica gel chromatography (19:1 CH2Cl2/MeOH) afforded 2 (753 mg, 97percent) as a pale yellow solid. (0105) m.p. 132-135° C. (MeOH) (0106) Rf=0.25 (silica gel, 19:1 CH2Cl2/MeOH) (0107) IR (neat) vmax 2750, 2358, 1646, 1616, 1487, 1296, 738 cm−1 (0108) 1H NMR (500 MHz, CDCl3) δ 7.33 (m, 5H), 7.11 (m, 4H), 5.05 (s, 2H), 3.89 (m, 4H), 3.67 (s, 2H), 3.32 (s, 2H), 2.68 (m, 2H), 2.51 (m, 2H), 2.40 (s, 3H) (0109) 13C NMR (150 MHz, CDCl3) δ 161.6, 153.4, 145.8, 137.7, 135.7, 134.4, 130.4, 129.3, 128.6, 127.5, 127.0, 126.0, 125.4, 102.1, 62.5, 50.7, 49.7, 48.3, 47.1, 43.3, 27.0, 19.4 (0110) HRMS (ESI-TOF) calcd. for C24H26N4OH+ [M+H] 387.2179, found 387.2166 |
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