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[ CAS No. 3939-01-3 ] {[proInfo.proName]}

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Chemical Structure| 3939-01-3
Chemical Structure| 3939-01-3
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Product Details of [ 3939-01-3 ]

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 :
Chemical Name :Methyl 1-benzyl-4-oxopiperidine-3-carboxylate hydrochloride

Calculated chemistry of [ 3939-01-3 ]

Physicochemical Properties

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

Pharmacokinetics

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

Lipophilicity

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

Druglikeness

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

Water Solubility

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

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.25

Safety of [ 3939-01-3 ]

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:

Application In Synthesis of [ 3939-01-3 ]

* 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.

  • Upstream synthesis route of [ 3939-01-3 ]
  • Downstream synthetic route of [ 3939-01-3 ]

[ 3939-01-3 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 3939-01-3 ]
  • [ 71486-53-8 ]
Reference: [1] European Journal of Organic Chemistry, 2014, vol. 2014, # 20, p. 4335 - 4341
[2] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 7, p. 1885 - 1892
  • 2
  • [ 3612-20-2 ]
  • [ 616-38-6 ]
  • [ 3939-01-3 ]
YieldReaction ConditionsOperation 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.
Reference: [1] Patent: EP1031575, 2000, A1,
[2] Patent: US2002/2283, 2002, A1,
  • 3
  • [ 793-19-1 ]
  • [ 3939-01-3 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 7, p. 1885 - 1892
  • 4
  • [ 100-46-9 ]
  • [ 3939-01-3 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 7, p. 1885 - 1892
  • 5
  • [ 24424-99-5 ]
  • [ 3939-01-3 ]
  • [ 161491-24-3 ]
YieldReaction ConditionsOperation 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.
Reference: [1] Patent: WO2004/96769, 2004, A1, . Location in patent: Page 21
[2] Patent: WO2004/2957, 2004, A1, . Location in patent: Page 44
  • 6
  • [ 3939-01-3 ]
  • [ 161491-24-3 ]
Reference: [1] European Journal of Organic Chemistry, 2014, vol. 2014, # 20, p. 4335 - 4341
  • 7
  • [ 38941-29-6 ]
  • [ 3939-01-3 ]
  • [ 1616632-77-9 ]
YieldReaction ConditionsOperation 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
Reference: [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 26, p. 6628 - 6631[2] Angew. Chem., 2014, vol. 126, # 26, p. 6746 - 6749,4
[3] Patent: US2017/107221, 2017, A1, . Location in patent: Paragraph 0104; 0105; 0106; 0107; 0108; 0109; 0110
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