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Chemical Structure| 5166-67-6 Chemical Structure| 5166-67-6

Structure of 5166-67-6

Chemical Structure| 5166-67-6

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Product Details of [ 5166-67-6 ]

CAS No. :5166-67-6
Formula : C9H17NO2
M.W : 171.24
SMILES Code : O=C(C1CN(C)CCC1)OCC
MDL No. :MFCD00006496
InChI Key :VFJJNMLPRDRTCO-UHFFFAOYSA-N
Pubchem ID :97981

Safety of [ 5166-67-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H227-H315-H319-H335
Precautionary Statements:P210-P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P370+P378-P403+P233-P403+P235-P405-P501

Computational Chemistry of [ 5166-67-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 0
Fraction Csp3 0.89
Num. rotatable bonds 3
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 51.36
TPSA ?

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

29.54 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.55
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

0.98
Log Po/w (WLOGP)?

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

0.51
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.

1.0
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

1.12
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.23

Water Solubility

Log S (ESOL):?

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

-1.32
Solubility 8.18 mg/ml ; 0.0477 mol/l
Class?

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

Very soluble
Log S (Ali)?

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

-1.19
Solubility 11.1 mg/ml ; 0.0648 mol/l
Class?

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

Very 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

-1.24
Solubility 9.92 mg/ml ; 0.0579 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.

-6.65 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)

2.2

Application In Synthesis of [ 5166-67-6 ]

* 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 [ 5166-67-6 ]

[ 5166-67-6 ] Synthesis Path-Downstream   1~28

  • 1
  • [ 614-18-6 ]
  • [ 5166-67-6 ]
  • 2
  • [ 108320-80-5 ]
  • [ 5166-67-6 ]
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  • [ 151-50-8 ]
  • [ 132462-25-0 ]
  • [ 132462-25-0 ]
  • 5
  • [ 5166-67-6 ]
  • [ 86685-14-5 ]
  • [ 114193-37-2 ]
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  • [ 5166-67-6 ]
  • [ 95-54-5 ]
  • [ 123771-24-4 ]
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  • [ 5166-67-6 ]
  • [ 4760-34-3 ]
  • [ 123771-25-5 ]
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  • [ 5166-67-6 ]
  • [ 140-88-5 ]
  • [ 121810-15-9 ]
  • 9
  • [ 5166-67-6 ]
  • [ 171819-57-1 ]
YieldReaction ConditionsOperation in experiment
73% The starting material was prepared as follows: (R)-Ethyl nipecotate (5.7 g 365 mmol), (prepared by resolution of ethyl nipecotate by treatment with L(+)-tartaric acid as described in J. Org. Chem. 1991, (56), 1168), was dissolved in 38.5% aqueous formaldehyde solution (45 ml) and formic acid (90 ml) and the mixture heated at reflux for 18 hours. The mixture was allowed to cool and added dropwise to cooled saturated aqueous sodium hydrogen carbonate solution. The mixture was adjusted to pH12 by addition of sodium hydroxide and the mixture was extracted with methylene chloride. The organic extract was washed with brine, dried (MgSO4) and the solvent removed by evaporation to give (R)-ethyl 1-methylpiperidine-3-carboxylate (4.51 g, 73%) as a colourless oil. MS-ESI: 172 [MH]+.
  • 11
  • 3-ethoxycarbonyl-1-methyl-pyridinium-<toluene-4-sulfonate> [ No CAS ]
  • [ 5166-67-6 ]
  • 12
  • [ 71962-74-8 ]
  • JandaJel-REM [ No CAS ]
  • [ 74-88-4 ]
  • [ 5166-67-6 ]
  • 13
  • [ 5166-67-6 ]
  • [ 882-33-7 ]
  • [ 470700-27-7 ]
  • 14
  • [ 50-00-0 ]
  • [ 71962-74-8 ]
  • [ 5166-67-6 ]
YieldReaction ConditionsOperation in experiment
Preparation 12 Ethyl 1-methylpiperidine-3-carboxylate 3 g of ethyl piperidine-3-carboxylate, 4 ml of aqueous formaldehyde, 300 mg of 10% Pd/C and 4 ml of glacial acetic acid are placed under an atmosphere of hydrogen (1 atm.) at 20 C. for 17 hours. After filtering off the catalyst over Celite and washing with 50 ml of ethanol, the solution is evaporated under reduced pressure and yields an oily residue. The residue is diluted with a mixture of toluene/water (1/1) and the pH is adjusted to 9 by adding 20% K2CO3. After separation of the two phases, the aqueous phase is extracted twice with toluene. The organic phases are washed with water, dried over Na2SO4 and yield a lightly coloured oil. Distillation under reduced pressure yields 2.4 g of the expected product. Boiling point: 105-110 C. (P=20 mmHg)
  • 15
  • [ 5166-67-6 ]
  • [ 4842-86-8 ]
  • 17
  • [ 5166-67-6 ]
  • [ 626-67-5 ]
  • [ 74-85-1 ]
  • [ 124-38-9 ]
  • 18
  • [ 5166-67-6 ]
  • [ 56060-42-5 ]
  • 19
  • [ 5166-67-6 ]
  • [ 28125-84-0 ]
  • 20
  • [ 5166-67-6 ]
  • [ 470700-28-8 ]
  • 21
  • [ 5166-67-6 ]
  • [ 111-84-2 ]
YieldReaction ConditionsOperation in experiment
With LiAlH4; In tetrahydrofuran; water; EXAMPLE 9 Reduction of Ethyl 1-methylnipecotate To a cooled solution of filtered or unfiltered LiAlH4 (2 mole) under argon was added <strong>[5166-67-6]ethyl 1-methylnipecotate</strong> (1 mole) in THF. After addition was complete, reaction was heated to 40 to 50 C. for 2 hr and then stirred overnight at room temperature. The reaction was quenched by adding H2O, and aqueous NaOH using cooling as required. The solution was then filtered and solids were washed with fresh THF. Yields were determined by GC analysis of crude filtered reaction solutions using nonane as an internal standard. Essentially no difference in yields was observed with filtered or unfiltered LiAlH4 solutions.
  • 22
  • [ 5166-67-6 ]
  • [ 205194-11-2 ]
YieldReaction ConditionsOperation in experiment
94% With sodium hydroxide; In tetrahydrofuran; water; A solution of (R)-<strong>[5166-67-6]ethyl 1-methylpiperidine-3-carboxylate</strong> (5.69 g, 33 mmol) in ether (20 ml) was added dropwise to a stirred solution of lithium aluminum hydride (36.6 ml of a 1M solution in THF, 36.6 mmol) in ether (85 ml) cooled to maintain a reaction temperature of 20 C. The mixture was stirred for 1.5 hours at ambient temperature and then water (1.4 ml), 15% aqueous sodium hydroxide solution (1.4 ml) and then water (4.3 ml) were added. The insolubles were removed by filtration and the volatiles removed from the filtrate by evaporation to give (R)-(1-methylpiperidin-3-yl)methanol (4.02 g, 94%) as a colourless oil. 1H NMR Spectrum: (DMSOd6) 1.06(q, 1H); 1.51-1.94(m, 5H); 2.04(s, 3H); 2.34(br s. 1H); 2.62(m, 1H); 2.78(d, 1H); 3.49(m, 1H); 3.59(m. 1H); MS-ESI: 130 [MH]+.
  • 23
  • [ 5166-67-6 ]
  • [ 345-35-7 ]
  • [ 136081-13-5 ]
YieldReaction ConditionsOperation in experiment
12.1 g (74.4%) With sodium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; ethyl acetate; Ethyl 1-methyl-3-(2'-fluorobenzyl-nipecotate To a solution of <strong>[5166-67-6]ethyl 1-methylnipecotate</strong> (10.0 g, 58.4 mmol) in dry tetrahydrofuran (350 ml) was added at -78 C. lithium bis(trimethylsilyl)amide (80.0 ml, 80.0 mmol) as a 1.0M solution in tetrahydrofuran and the resulting solution was allowed to stir at -78 C. for 3 hours. To this was added 2-fluorobenzylchloride (7.0 ml, 8.5 g, 59 mmol) and the resulting solution was allowed to warm to room temperature over 5 hours. Thin-layer chromatography showed reaction was not complete. More 2-fluorobenzylchloride (20 ml, 2.4 g, 17 mmol) was added to the reaction mixture and the resulting solution was allowed to stir overnight, ca. 18 hours. The tetrahydrofuran was removed by evaporation in vacuo and the orange residue was dissolved in ethyl acetate. The organic solution was extracted with 0.5N HCl (4*100 ml) and the aqueous acid extracts were combined and made basic with 10N NaOH. The aqueous was then extracted with ethyl acetate (5*100 ml) and the combined extracts were dried over MgSO4 and concentrated to yield 12.1 g (74.4%) of ethyl 1-methyl-3-(2'-fluoro)-benzyl-nipecotate as an orange oil. 1 H-NMR (CDCl3) delta: 7.22-7.15 (m, 1H), 7.10-6.95 (m, 3H), 4.14-4.05 (m, 2H), 3.01 (bd, 1H, J=10.3 Hz), 2.87 (s, 2H), 2.58 (bd, 1H, J=10.3 Hz), 2.24 (s, 3H), 2.04-1.95 (m, 3H), 1.69-1.60 (m, 2H), 1.30-1.22 (m, 1H), 1.16 (t, 3H, J=7.1 Hz).
  • 24
  • [ 71962-74-8 ]
  • [ 74-88-4 ]
  • [ 5166-67-6 ]
YieldReaction ConditionsOperation in experiment
In acetone; at 20℃; N-Methyl-ethyl nipecotate (85):Ethyl nipecotate (5.0 g, 0.032 mol) was dissolved in acetone (50 niL). Methyl iodide (3 mL, 0.048 mol) was added dropwise over 1 hour and the mixture was stirred at room temperature for 1 hour. The mixture was concentrated to remove acetone and partitioned between saturated sodium bicarbonate (50 mL) and ethyl acetate (1 x 5OmL). The aqueous layer was extracted with an additional 2 x 50 mL ethyl acetate. The combined organics were washed with 2 x 50 mL water, 1 x 50 mL saturated sodium chloride, and dried over Na2SO4. The dried organics were evaporated to 1.43 g of oil. The material was used without further purification. MS (ESI) m/z 172 [M+H]+.
Example 19: Synthesis of 3-Methyl-5-(l-methylpiperidin-3-yl)-l,2,4-oxadiazole; [00322] N-Methyl-ethyl nipecotate (4c):Ethyl nipecotate (5.0 g, 0.032 mol) was dissolved in acetone (50 mL). Methyl iodide (3 mL, 0.048 mol) was added dropwise over 1 hour and the mixture was stirred at roomtemperature for 1 hour. The mixture was concentrated to remove acetone and partitioned between saturated sodium bicarbonate (50 mL) and ethyl acetate (1 x 50mL). The aqueous layer was extracted with an additional 2 x 50 mL ethyl acetate. The combined organics were washed with 2 x 50 mL water, 1 x 50 mL saturated sodium chloride, and dried over a2S04. The dried organics were evaporated to an oil to obtain 1.43 g. The material was used without further purification. MS (ESI) m/z 172 [M+H]+.
In acetone; at 20℃; for 2h; Ethyl nipecoiate (5.0 g, 0.032 mol) was dissolved in acetone (50 mL). Methyl iodide (3 rnL, 0.048 mol) was added dropwise over 1 hour and the mixture was stirred at room temperature for 1 hour. The mixture was concentrated to remove acetone and partitioned between saturated sodium bicarbonate (50 mL) and ethyl acetate (I x SOmL). The aqueous layer was extracted with an additional 2 * 50 mL ethyl acetate. The combined organics were washed with 2 x 50 mL water, 1 chi SO mL saturated sodium chloride,were evaporated to an oil to obtain 1.43 g. The material was used without further purification. MS (ESi) m/z 172 [M+H]-h
  • 25
  • [ 5166-67-6 ]
  • [ 118493-85-9 ]
  • [ 129595-04-6 ]
YieldReaction ConditionsOperation in experiment
With sodium methylate; In tetrahydrofuran; for 2h;Reflux; 3-Methyl-5-(l-methylpiperidin-3-yl)-l,2,4-oxadiazole (86):N-methyl-ethyl nipecotate (85) (0.7 g, 0.0041 mol) and acetamide oxime (0.75g, 0.0102 mol) were dissolved in 30 mL tetrahydrofuran. Sodium methoxide (1.Ig9 0.0205 mol) was added and the mixture was heated at reflux for 2 hours. The mixture was concentrated to remove THF and partitioned between water (25 mL) and dichloromethane (1 x 25 mL). The aqueous layer was extracted with an additional 2 x 25 mL dichloromethane. The combined organics were washed with 1 x 50 mL saturated sodium chloride, and dried over Na2SO4. The dried organics were evaporated to an oil. The residue was chromatographed with 5 g silica gel, 5% methanol/ethyl acetate, to obtain 0.51 g of the free base. Hydrochloric acid in ethanol (2.5 M) (1.6 mL, 0.011 mol) was added and the mixture was concentrated to dryness. Crystallization from ethanol/MTBE afforded 436 mg of 86 as white solid. MS (ESI) m/z 182 [M+H]+. 1H NMR (DMSO-d6) delta 1.59-1.66 (m, 1 H), 1.88-1.98 (s, 2 H), 2.17-2.20 (d, IH), 2.34 (s, 3 H), 2.77 (s, 3 H), 2.92-2.95 (m, 1 H), 3.18-3.21 (m, 1 H), 3.37-3.47, (d, IH), 3.60- 3.78, (m, 2H).
With sodium methylate; In tetrahydrofuran; for 2h;Reflux; 3-Methyl-5-(l -methylpiperidin-3-yl)-l ,2,4-oxadiazole (5c):I-N-methyl-ethyl nipecotate (4c) (0.7 g, 0.0041 mol) and acetamide oxime (0.75g, 0.0102 mol) were dissolved in 30 mL tetrahydrofuran. Sodium methoxide (l . l g, 0.0205 mol) was added and the mixture was heated at reflux for 2 hours. The mixture was concentrated to remove THF and partitioned between water (25 mL) and dichloromethane (1 x 25 mL). The aqueous layer was extracted with an additional 2 x 25 mL dichloromethane. The combined organics were washed with 1 chi 50 mL saturated sodium chloride, and dried over Na2SC>4. The dried organics were evaporated to an oil. The residue was chromatographed with 5 g silica gel, 5% methanol/ethyl acetate, to obtain 0.51 g of the free base. Hydrochloric acid in ethanol (2.5 M) (1.6 mL, 0.01 1 mol) was added and the mixture was concentrated to dryness. Crystallization from ethanol/MTBE afforded 436 mg white solid. MS (ESI) m/z 182 [M+H]+. NMR (DMSO-d6) 5 1.59- 1.66 (m, 1 H), 1.88- 1.98 (s, 2 H), 2.17-2.20 (d, 1 H), 2.34 (s, 3 H), 2.77 (s, 3 H), 2.92-2.95 (m, 1 H), 3.18-3.21 (m, 1 H), 3.37- 3.47, (d, 1H), 3.60-3.78, (m, 2H).
  • 26
  • [ 5166-67-6 ]
  • [ 118493-85-9 ]
  • [ 114724-58-2 ]
YieldReaction ConditionsOperation in experiment
S -N-Boe -ethyl nlpeeotate (.) (0,7 g, 0.0041 mol) and aceiamide oxirne (0.75g, 0.0102 mol) were. dissolved in 30 mL teirahydrofuran. Sodium methoxide (l.lg, 0.0205 mol) was added and. the mixture was heated at reflux for 2 hours. The mixture was concentrated to remove THF and partitioned between water (25 mL) and dichloromethane ( I x 25 mL). The aqueous layer was extracted with an additional 2 x 25 mL dichioromethane. The combined organics were washed with I< 50 mL saturated, sodium chloride, and dried over Nag&O . The dried organics were evaporated to an oil. The residue was chromatogra;phed with 5 g silica gel, 5% raethano./ethyl acetate, to obtain 0.51 g of the tree base. Hydrochloric acid in ethanol (2.5 M) (1.6 mL, 0.01 1 mol) was added and the mixture was concentrated to dryness. Crystallization fromethanol/ 'IBE fforded 436 mg white solid. MB (ESI) mlz 182 [ +B]. hi NM (DMSO-46) 5 1.59-1.66 (m, I H), 1.8.8.- 1.98 (s, 2 H), 2.17-2.20 (d, 1H), 234 (s, 3 H), 2.77 (s, 3 H), 2.92- 2.95 (m, 1 H), 3.18-3.21 (m, 1 H% 337-3.47, (d, 1H), 3.60-3.78, (m, 2H).
  • 27
  • [ 5166-67-6 ]
  • [ 126145-44-6 ]
  • 1-((5-(1-methylpiperidin-3-yl)-1,2,4-oxadiazol-3-yl)methyl)pyrrolidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
36% With sodium hydride; In tetrahydrofuran; mineral oil;Inert atmosphere; Schlenk technique; Molecular sieve; Reflux; General procedure: 1-(2-Oxopyrrolidin-1-yl)acetamidoxime (2.40 equiv) was stirred in dry THF with 4A MS for 1 h, and NaH (60% inoil, 3.0 equiv) was added and stirred for 50 mins and then heated at 50 C for 30 min. A solution of an ester 5a~f (1.0 equiv) in THF was added dropwise and the reaction mixture was heated under reflux for 1.5 h. After cooling, solvent was removed from the reaction mixture and the residue was extracted with CH2Cl2. The organic extract was concentrated in vacuo, and the residue was purified by column chromatography on silica gel using chloroform/methanol (30:1~10:1) as eluent to obtain the corresponding compound 6a~f.
  • 28
  • [ 122-51-0 ]
  • [ 71962-74-8 ]
  • [ 5166-67-6 ]
YieldReaction ConditionsOperation in experiment
90% With platinum on carbon; hydrogen; toluene-4-sulfonic acid; at 120℃; under 30003.0 Torr; for 0.2h;Inert atmosphere; Autoclave; General procedure: An autoclave was filled with catalyst (1 mol% based on the molar amount of amine), flushed with argon and topped up with a solution of amine (0.1 mol) and orthocarboxylic acid ester (0.11-0.3mol) in 10 ml of methanol (or ethanol) and 0.5 ml of a 0.2 M solution of anhydrous ptoluenesulphonic acid in methanol (or ethanol). The mixture was heated to 120C and hydrogen was injected to 40 bar and then the mixture was stirred at a constant pressure until hydrogen absorption could no longer be detected (0.2 - 6 h). After being filtered off from the catalyst, the filtrate was distilled.
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 5166-67-6 ]

Esters

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Related Parent Nucleus of
[ 5166-67-6 ]

Piperidines

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