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[ CAS No. 532-12-7 ] {[proInfo.proName]}

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Chemical Structure| 532-12-7
Chemical Structure| 532-12-7
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Product Details of [ 532-12-7 ]

CAS No. :532-12-7 MDL No. :MFCD00052019
Formula : C9H10N2 Boiling Point : -
Linear Structure Formula :- InChI Key :DPNGWXJMIILTBS-UHFFFAOYSA-N
M.W : 146.19 Pubchem ID :442649
Synonyms :

Calculated chemistry of [ 532-12-7 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 48.52
TPSA : 25.25 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.77 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.85
Log Po/w (XLOGP3) : 0.6
Log Po/w (WLOGP) : 1.28
Log Po/w (MLOGP) : 0.78
Log Po/w (SILICOS-IT) : 3.11
Consensus Log Po/w : 1.52

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.46
Solubility : 5.05 mg/ml ; 0.0345 mol/l
Class : Very soluble
Log S (Ali) : -0.7
Solubility : 28.9 mg/ml ; 0.198 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.15
Solubility : 0.105 mg/ml ; 0.000716 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.22

Safety of [ 532-12-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 532-12-7 ]

* 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 [ 532-12-7 ]

[ 532-12-7 ] Synthesis Path-Downstream   1~79

  • 1
  • [ 532-12-7 ]
  • [ 563-41-7 ]
  • 4-amino-1-[3]pyridyl-butan-1-one semicarbazone; hydrochloride [ No CAS ]
  • 2
  • [ 532-12-7 ]
  • [ 59-88-1 ]
  • 4-amino-1-[3]pyridyl-butan-1-one-phenylhydrazone; hydrochloride [ No CAS ]
  • 3
  • [ 532-12-7 ]
  • [ 93-97-0 ]
  • <i>N</i>-(4-oxo-4-[3]pyridyl-butyl)-benzamide [ No CAS ]
  • 4
  • [ 532-12-7 ]
  • [ 93-97-0 ]
  • 1-benzoyl-5-[3]pyridyl-2,3-dihydro-pyrrole [ No CAS ]
  • 6
  • [ 532-12-7 ]
  • <i>N</i>-(4-oxo-4-[3]pyridyl-butyl)-benzamide [ No CAS ]
  • 7
  • [ 532-12-7 ]
  • 4-amino-1-[3]pyridyl-butan-1-one oxime ; hydrochloride [ No CAS ]
  • 8
  • [ 532-12-7 ]
  • [ 5746-86-1 ]
YieldReaction ConditionsOperation in experiment
84.7% With hydrogen;palladium 10% on activated carbon; In methanol; for 5h; D. Preparation of Nornicotine: Myosmine (32 g, 0.219 mol) was dissolved in 150 ml of methanol and hydrogenated at atmospheric pressure with 1.3 g of 10% palladium on carbon as catalyst. After 5 hours the mixture was filtered and the filtrate was concentrated to get a brown solid (32 g, 94.9% purity by GC). It was further purified by vacuum distillation at 0.1 mm Hg to get pure nornicotine (27.46 g, 84.7% yield, 97.5% purity by GC). 1H NMR (CDCl3): delta 1.66-2.72 (2H,m), 3.0 (2H,m), 4.13 (1H,t), 7.24 (1H,m), 7.69 (1H, dt), 8.46 (1H,dd), and 8.59 (1H,d). 13C-NMR (CDCl3): delta 148.4, 148.1, 140.16, 134.1, 123.3, 60.0, 46.8, 34.2, and 25.4. IR: 3291, 2960, 1641, 1578 Cm-1.
With palladium 10% on activated carbon; hydrogen; In ethanol; for 12h;Large scale; The total crude Myosamine (from above) was takenup in 16 E ethanol, and 250 grams of 10% palladium on carbon was added and then resulting mixture, was stirred under hydrogen atmosphere for 12 hours, then filtered using celite, and washed with ethanol. The ethanol was removed using vacuum to give a dark brown non-viscous oil
The total crude Myosamine (from above) was taken up in 16 L methanol and 4 L of acetic acid, and the resulting solution was cooled to an internal temperature of -40 degrees centigrade, then 700 grams of sodium borohydride (granular) was added in portions over 1 hout The reaction was let warm to room temperature with stirring, and then submitted to vacuum distillation to remove most of the solvent. The resulting liquor was added 25 L of watet This was brought to pH>10 with NaOH. This was extracted three times with 15 L of dichloromethane, and the combined extracts were submitted to medium vacuum distillation to give a crude non-viscous dark brown colored oil.
With sodium tetrahydroborate; acetic acid; In methanol; at 20℃;Cooling with ice; General procedure: To a solution of substituted benzoic acid 3a-h (0.07 mol) inabsolute ethyl alcohol (100 mL) was slowly added thionyl chloride (15 mL). The mixture was heated to reflux for 2 h, and then cooledto room temperature. The solvent was removed and the solid residuewas dissolved in ethyl acetate (100 mL), and washed withsaturated NaHCO3 solution (100 mL 2). The organic layer wasdried and concentrated to give the intermediates 4a-h as paleyellow oily matter in 94.4e99.4% yield. They were used in the nextstep without additional purification.To a solution of NaH (5.6 g, 0.14 mol, 60%) in anhydrous THF(250 mL) was added 4a-h (0.07 mol) under the mechanical agitation.After heating to 60 C, N-Vinylpyrrolidone (0.07 mol) wasadded by dropwise and the mixture was heated to 72 C for 3 h.Then the reaction mixture was cooled to room temperature, thenpoured into ice water (500 mL), extracted with ethyl acetate(100 3 mL), and washed with saturated NH4Cl solution (300 mL)and brine (300 mL). The organic layer was dried and concentratedto give the intermediates 5a-h as brown oily matter in 82.3e94.2%yield, which was used in the next step without additionalpurification.A solution of 5a-h (0.06 mol) in THF (15 mL) was added to the5 N HCl (60 mL) under reflux. After the reaction mixture wasrefluxed for 3e5 h, then the reaction mixture was cooled to roomtemperature and concentrated in vacuo to remove the solvent THF.The pH was adjusted to 11 with saturated NaOH solution, thenextracted with ethyl acetate (100 mL 3), and washed with brine(150 mL 2). The organic layer was dried and concentrated to givethe intermediates 6a-h as brown oily matter in 82.8e87.2% yield,which was used in the next step without additional purification.To a solution of 6a-h (0.05 mol) in methanol (80 mL) was addedacetic acid two drops, and then NaBH4 (3.8 g, 0.1mol) was addedslowly under the condition of ice salt bath. After reaction at roomtemperature for 3 h, the solvent was removed and the residue wasdissolved in water. The pH was adjusted to 1 with 6 N HCl, washedwith methyl tertiary butyl ether (50 mL 3), and then the pH wasadjusted to 12 with NaOH solution. The mixturewas extracted withdichloromethane (100 mL 3), and washed with brine(150 mL 2). The organic layer was dried and concentrated to givethe brown oil, which was dissolved in acetone to form oxalic acidsalt. Intermediates 7a-h were obtained as white solid in42.3e55.6% yield.
With palladium 10% on activated carbon; hydrogen; In ethanol; under 38002.6 Torr; for 12h;Large scale; A solution of N-vinyl pyrrolidinone (4.5kg) in 2.5Kg of toluene was added to 2.5 Kg of Sodium Hydride (60% dispersion in mineral oil) as a stirred suspension in 20L of toluene. The resulting mixture was stirred for about 15 minutes at room temperature. 5Kg of ethyl nicotinate in 10Kg of toluene was added to the resulting mixture in portions and by a constant slow stream of liquor (light golden color). The exothermic reaction was controlled at an internal temperature of about 60C by controlling the rate of addition of the ethyl nicotinate - toluene solution. After addition of about one third of the ethyl nicotinate, a green precipitate was formed. After addition was completed, the green heterogeneous mixture was heated to an internal temperature of about 85 C and maintained at this temperature for about 12 hours. The resulting solution was injected into a precooled solution of 30L of 4N HCI at 0C followed by vigorous stirring for about 5 minutes. The layers were separated, and the toluene layer was washed once with 2.5Kg of 4N HCI. 8L of concentrated HCI was added to the combined acidic aqueous layers, and the reaction mixture was heated to boiling and maintained at this temperature for about 3 hours (or until the reaction was completed, as determined by thin layer chromatography (TLC)). The reaction mixture was cooled to 0C, and then neutralized with 50% sodium hydroxide solution while not allowing the internal temperature to go above 35 to 40 degrees centigrade. The pH was made very basic by addition of a sodium hydroxide solution (50%) until the pH reached 1 1 to 13 (as indicated by a blue color change on litmus paper). The resulting solution was extracted 4 times with 15L of dichloromethane, and the combined extracts were subjected to medium vacuum distillation to yield myosamine as a non-viscous brownish oil. (0138) [0081] 40L of anhydrous ethanol was added to the crude myosamine product, and the resulting solution was added to 2Kg of 10% palladium-on-carbon. The resulting mixture was subjected to hydrogen pressure of 50 atm. The reaction was completed within 12 hours. The resulting heterogeneous mixture was filtered through celite, and then washed twice with 10L of ethanol. The combined ethanolic solutions of the crude nornicotine product was subjected to vacuum distillation (29 inches Hg) at below 50C, and then the crude dark brown oil was taken up in 10L water. A solution of 5L of formaldehyde solution (37%) with 4L of formic acid (85%) was added to the resulting solution, and the mixture was heated to an internal temperature of 90 C and maintained at this temperature for 20 hours. The reaction mixture was cooled to -5 C, and then made basic (i.e., a pH greater than 10) by addition of a sodium hydroxide solution (50%). The basic liquor was then extracted 3 times with 15L of dichloromethane, and the combined extracts were subjected to med vacuum distillation to yield crude RS-Nicotine product as a dark brown oil. The dark brown oil was high vacuum distilled twice to yield RS-Nicotine having a purity that meets the requirements of the USP purity test.
With palladium 10% on activated carbon; hydrogen; In ethanol; under 19001.3 Torr; for 6h; Synthesis Example 1-R,S Nicotine Synthesis (0094) 1 equivalent of potassium hydride was added to a stirred solution of 1-vinyl-2-pyrrolidinone (2) in dry THF under a nitrogen atmosphere. The reaction mixture was stirred at room temperature for about 20 minutes, then ethyl nicotinate (1 equivalent) was added and the resulting mixture was stirred for 24 hours at 65 degrees centigrade. The reaction was cooled and then acidified with 5% HCl, and then concentrated HCl was added and the resulting solution was refluxed for 48 hours. The pH was adjusted to 13 with sodium hydroxide, and the aqueous and organic layers of the resulting biphasic solution were separated three times using equal volumes of dichloromethane. The combined extracts from the separation were dried over sodium sulfate, filtered and the solvent evaporated to give an amorphous material. The amorphous material was taken up in 3 parts ethanol, and then palladium-on-carbon was added (about 10%) and the resulting mixture was subjected to hydrogen pressure for 6 hours (greater than 25 atmospheres). The resulting residue was diluted with more ethanol and filtered through celite. The solvent was evaporated to dryness under vacuum with minimal heat, and then the residue was taken up in a formic acid/formaldehyde solution (1:1). The resulting mixture was heated to an internal temperature of 90 degrees Celsius and maintained at this temperature over a period of 12 hours, and then cooled and neutralized with sodium hydroxide to a pH of greater than 10, and then extracted with dichloromethane and dried over sodium sulfate, filtered and concentrated to give a brown oil. This oil was vacuum distilled to give pure RS Nicotine.
With sodium tetrahydroborate; In isopropyl alcohol; at 20℃; 1.0 eq. of ethyl nicotinate, toluene, 1.6 eq. of sodium ethoxide, and 1.2 eq. of i-vinyl-2-pyrrolidone (NVP) were charged into a flask at room temperature of about 20C under anhydrous conditions. Then the reaction was run at 100C for 3 hours. The reaction was completed, and after the mixture had been cooled down to 30C, 695.0 g HCI (36% by weight in water) was added dropwise. The low boiling components like acetaldehyde, ethanol and the gaseous CO2 were removed by distillation, together with parts of the toluene and the water. When the reaction temperature reached 105C, distillation was stopped and the reaction mixture was stirred at a temperature between 100C and 105C overnight. After completion of the reaction, the pH was adjusted to a value between 9.5 to 10.5 using NaOH (30% by weight in water). 360.0 g iso propanol and 1.0 eq. of NaBH4 (in respect of the ethyl nicotinate) were charged into the reaction vessel. The reaction was run at room temperature (about 20C) for more than 3 hours (at this point the content of myosmine was below 3.0% by weight). 2.0 eq. of formic acid (HCOOH, in respect of the ethyl nicotinate) and 1.2 eq. paraformaldehyde ((HCHO)n, in respect of the ethyl nicotinate) were added and the mixture was stirred at 65C for at least 3 hours. After the reaction was finished (at this point the content of myosmine was below 0.5% by weight), the pH of the mixture was adjusted to a value of 13 to 14 using NaOH (30% by weight in water). Water was added until all inorganic solids were dissolved. The mixture was extracted twice with toluene. The combined organic phases were concentrated to obtain the crude product. By distillation of the crude product, racemic nicotine was obtained as a colorless oil with a purity of 98.9% (yield was 66.0%) as sample 1.
With sodium tetrahydroborate; isopropyl alcohol; at 10℃; General procedure: Iso-propanol (29.0 g, as given in Table 1a) and 1.0 eq. of NaBH4 (in respect of the ethyl nicotinate) were charged in portions during 1 hour into the reaction vessel. The reaction was run at about 10C for more than 3 hours (at this point the content of myosmine was below 3.0% by weight).

  • 9
  • [ 614-18-6 ]
  • [ 2399-66-8 ]
  • [ 141-52-6 ]
  • [ 71-43-2 ]
  • [ 532-12-7 ]
  • 10
  • [ 614-18-6 ]
  • [ 2399-66-8 ]
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  • 11
  • [ 98953-15-2 ]
  • [ 532-12-7 ]
  • 12
  • [ 109700-79-0 ]
  • [ 532-12-7 ]
  • 15
  • [ 54-11-5 ]
  • [ 1121-55-7 ]
  • [ 536-78-7 ]
  • [ 532-12-7 ]
  • [ 487-19-4 ]
  • 16
  • [ 532-12-7 ]
  • [ 77287-34-4 ]
  • [ 85324-02-3 ]
  • 17
  • [ 532-12-7 ]
  • [ 407-25-0 ]
  • (R)-(+)-N-Trifluoroacetyl-2-(3-pyridinyl)pyrrolidine [ No CAS ]
  • (S)-(-)-N-Trifluoroacetyl-2-(3-pyridinyl)pyrrolidine [ No CAS ]
  • 18
  • [ 532-12-7 ]
  • [ 2258-42-6 ]
  • [ 54-11-5 ]
  • [ 25162-00-9 ]
  • 19
  • [ 532-12-7 ]
  • [ 2258-42-6 ]
  • [ 38840-03-8 ]
  • (R)-(+)-N-Formylnornicotinel [ No CAS ]
  • 20
  • [ 532-12-7 ]
  • [ 75195-77-6 ]
  • 22
  • (4-Oxo-4-pyridin-3-yl-butyl)-carbamic acid tert-butyl ester [ No CAS ]
  • [ 532-12-7 ]
  • 24
  • [ 36740-10-0 ]
  • [ 532-12-7 ]
  • [ 5746-86-1 ]
  • 25
  • Isopropyl-[1-pyridin-3-yl-4-(2,2,5,5-tetramethyl-[1,2,5]azadisilolidin-1-yl)-but-(E)-ylidene]-amine [ No CAS ]
  • [ 532-12-7 ]
  • 26
  • [ 22083-74-5 ]
  • [ 532-12-7 ]
  • [ 525-74-6 ]
  • [ 487-19-4 ]
  • [ 15569-85-4 ]
  • 3-(1-Methyl-2,3-dihydro-1H-pyrrol-2-yl)-pyridine [ No CAS ]
  • 28
  • [ 100-54-9 ]
  • 1-(3-bromopropyl)-2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane [ No CAS ]
  • [ 532-12-7 ]
  • 29
  • [ 532-12-7 ]
  • [ 107-92-6 ]
  • [ 224569-62-4 ]
  • 4-propylmyosmine [ No CAS ]
  • 2-propylmyosmine [ No CAS ]
  • 2,6-dipropylmyosmine [ No CAS ]
  • 31
  • [ 98953-15-2 ]
  • [ 64-17-5 ]
  • Raney nickel [ No CAS ]
  • [ 532-12-7 ]
  • 32
  • [ 7647-01-0 ]
  • [ 532-12-7 ]
  • palladium/charcoal [ No CAS ]
  • platinum [ No CAS ]
  • [ 1772-29-8 ]
  • 3-pyrrolidin-2-yl-piperidine [ No CAS ]
  • 33
  • [ 532-12-7 ]
  • [ 64-17-5 ]
  • palladium [ No CAS ]
  • [ 5746-86-1 ]
  • 34
  • [ 532-12-7 ]
  • [ 64-17-5 ]
  • [ 64-19-7 ]
  • zinc-powder [ No CAS ]
  • [ 5746-86-1 ]
  • 35
  • [ 532-12-7 ]
  • [ 858262-19-8 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; palladium on activated charcoal; platinum Hydrogenation; isomer(ic) II;
  • 36
  • [ 532-12-7 ]
  • [ 858262-19-8 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; palladium on activated charcoal; platinum Hydrogenation; isomer(ic) I;
  • 37
  • [ 532-12-7 ]
  • [ 59578-62-0 ]
  • [ 80508-23-2 ]
  • 38
  • [ 123-75-1 ]
  • [ 1120-90-7 ]
  • [ 110-86-1 ]
  • [ 532-12-7 ]
  • 39
  • [ 88-12-0 ]
  • [ 614-18-6 ]
  • [ 532-12-7 ]
YieldReaction ConditionsOperation in experiment
10037] Sodium hydride (1.25 Kg, 31.2 mole) was added to a stirred solution of toluene (10 L) under inert atmosphere (dry nitrogen or argon gas) and this was let stir for about 15 minutes at room temperature. Then, a solution of n-vinyl pyrrolidinone (2kg, 18.02 mole) in 1 L of toluene was added over 15 minutes via addition flannel, and the resulting mixture let stir at ambient temperature for about 15 minutes. Then a solution of ethyl nicotinate (2.5 Kg, 16.56 mole) in 2 L toluene was added in portions over a two hour period. The mildly effervescent exothermic reaction mixture turned a light rose color and then a light green ppt formed as the exothermic reaction maintained itself at about 60-65C. After addition was complete, the reaction mixture was heated to 85 C. for about 16 hours, then cooled to room temperature yielding a greenish heterogeneous mixture. (NOTE: this mixture is flows well and is able to be pumped through ? PE tubing with diaphragm pump with facility.) This mixture is added, in about 250 mE portions, to 25 E of a boiling solution of 6N HC1. (NOTE: The addition takes place with vigorous effervescence, which subsides within a few minutes after addition of the aliquot of reaction mixture to the hot HC1.) After all the reaction mixture has been added, the resulting dark brown biphasic mixture was stirred under reflux for an additional hout Then, the reaction was cooled, and the layers separated. The aqueous layer was cooled, and made basic (pH>1 0) with NaOH (50%), then extracted 3x8 E of dichloromethane, and the solvent removed via vacuum distillation (T bath=ca.45 degrees centigrade) to yield a dark brown, non-viscous oil.
A solution of N-vinyl pyrrolidinone (4.5kg) in 2.5Kg of toluene was added to 2.5 Kg of Sodium Hydride (60% dispersion in mineral oil) as a stirred suspension in 20L of toluene. The resulting mixture was stirred for about 15 minutes at room temperature. 5Kg of ethyl nicotinate in 10Kg of toluene was added to the resulting mixture in portions and by a constant slow stream of liquor (light golden color). The exothermic reaction was controlled at an internal temperature of about 60C by controlling the rate of addition of the ethyl nicotinate - toluene solution. After addition of about one third of the ethyl nicotinate, a green precipitate was formed. After addition was completed, the green heterogeneous mixture was heated to an internal temperature of about 85 C and maintained at this temperature for about 12 hours. The resulting solution was injected into a precooled solution of 30L of 4N HCI at 0C followed by vigorous stirring for about 5 minutes. The layers were separated, and the toluene layer was washed once with 2.5Kg of 4N HCI. 8L of concentrated HCI was added to the combined acidic aqueous layers, and the reaction mixture was heated to boiling and maintained at this temperature for about 3 hours (or until the reaction was completed, as determined by thin layer chromatography (TLC)). The reaction mixture was cooled to 0C, and then neutralized with 50% sodium hydroxide solution while not allowing the internal temperature to go above 35 to 40 degrees centigrade. The pH was made very basic by addition of a sodium hydroxide solution (50%) until the pH reached 1 1 to 13 (as indicated by a blue color change on litmus paper). The resulting solution was extracted 4 times with 15L of dichloromethane, and the combined extracts were subjected to medium vacuum distillation to yield myosamine as a non-viscous brownish oil. (0138) [0081] 40L of anhydrous ethanol was added to the crude myosamine product, and the resulting solution was added to 2Kg of 10% palladium-on-carbon. The resulting mixture was subjected to hydrogen pressure of 50 atm. The reaction was completed within 12 hours. The resulting heterogeneous mixture was filtered through celite, and then washed twice with 10L of ethanol. The combined ethanolic solutions of the crude nornicotine product was subjected to vacuum distillation (29 inches Hg) at below 50C, and then the crude dark brown oil was taken up in 10L water. A solution of 5L of formaldehyde solution (37%) with 4L of formic acid (85%) was added to the resulting solution, and the mixture was heated to an internal temperature of 90 C and maintained at this temperature for 20 hours. The reaction mixture was cooled to -5 C, and then made basic (i.e., a pH greater than 10) by addition of a sodium hydroxide solution (50%). The basic liquor was then extracted 3 times with 15L of dichloromethane, and the combined extracts were subjected to med vacuum distillation to yield crude RS-Nicotine product as a dark brown oil. The dark brown oil was high vacuum distilled twice to yield RS-Nicotine having a purity that meets the requirements of the USP purity test.
1.2 equivalent of sodium hydride was added to a stirred solution of 1-vinyl-2-pyrrolidinone (2) in dry THF/DMF (3/1) under a nitrogen atmosphere. The reaction mixture was stirred at room temperature for about 20 minutes, then ethyl nicotinate (1 equivalent) was added, and the resulting mixture was stirred for 24 hours at 65 degrees centigrade. The reaction was cooled and then acidified with 5% HCl, and then concentrated HCl was added, and the resulting mixture was refluxed for 48 hours. The pH was adjusted to 6 with sodium hydroxide, and then excess dichloromethane was added and the layers were separated. The aqueous layer was extracted twice with excess dichloromethane, and the extracts were combined and washed with water, and then dried over sodium sulfate. The solution was then filtered and the solvent removed using vacuum to yield a brownish solid. This solid was dissolved in ethanol (about 5 to about 10 parts), and then 0.5 parts palladium on carbon was added and the resulting mixture was subjected to hydrogen pressure for 6 hours (greater than 25 atmospheres). The resulting residue was diluted with more ethanol and filtered through celite. The solvent was evaporated to dryness under vacuum with minimal heat, and then the residue was taken up in 3 parts formic acid and 3 parts formaldehyde, and the resulting solution was heated to an internal temperature of about 90 to about 95 degrees centigrade and maintained at this temperature over a period of 24 hours. The reaction was cooled and then vacuum distilled to yield pure RS nicotine as a clear, colorless non-viscous oil.
  • 41
  • [ 532-12-7 ]
  • 2-propyl-5-pyrrolidin-2-yl-pyridine [ No CAS ]
  • 42
  • [ 532-12-7 ]
  • (+/-)-6-n-propyl-3-(1-methyl-2-pyrrolidinyl)pyridine [ No CAS ]
  • 43
  • Isopropyl-[1-pyridin-3-yl-eth-(E)-ylidene]-amine [ No CAS ]
  • [ 532-12-7 ]
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  • [ 350-03-8 ]
  • [ 532-12-7 ]
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  • [ 6293-82-9 ]
  • [ 532-12-7 ]
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  • [ 104501-58-8 ]
  • [ 532-12-7 ]
  • 47
  • Dimethyl-((E)-3-pyridin-3-yl-3-trimethylsilanyloxy-allyl)-amine; hydriodide [ No CAS ]
  • [ 532-12-7 ]
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  • [ 532-12-7 ]
  • [ 75195-78-7 ]
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  • [ 532-12-7 ]
  • [ 75195-79-8 ]
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  • [ 532-12-7 ]
  • [ 75195-74-3 ]
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  • [ 532-12-7 ]
  • [ 85324-03-4 ]
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  • [ 532-12-7 ]
  • [ 85324-04-5 ]
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  • [ 60573-68-4 ]
  • [ 532-12-7 ]
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  • [ 54950-20-8 ]
  • [ 532-12-7 ]
  • 60
  • [ 532-12-7 ]
  • [ 81290-20-2 ]
  • [ 1262380-96-0 ]
YieldReaction ConditionsOperation in experiment
68% With potassium hydrogenfluoride; trifluoroacetic acid; In acetonitrile; at 0 - 20℃; General procedure: Keeping the temperature at about 0 C, trifluoroacetic acid (0.95 mL, 12.5 mmol), KHF2 (585 mg, 7.5 mmol), and trifluoromethyltrimethylsilane (1.9 mL, 12.5 mmol) were successively added to a solution of the corresponding imine 1, 2 or 3 (10 mmol) in dry acetonitrile (50 mL). After stirring for 12 h at rt, the solvent was gently evaporated under reduced pressure, the residue was quenched with saturated aqueous NaHCO3 (50 mL) and extracted with ether (3×10 mL). The combined extract was dried over Na2SO4, the solvent was evaporated at reduced pressure and the residue was purified by column chromatography on silica gel eluting with a 20/1 mixture of hexane/ethyl acetate. This afforded the tagged amine. In the case of volatile amines 4a, 4d, 5a, 6a, 8a, and 8b the combined extract was mixed with hydrochloric acid (1.5 mL), evaporated to dryness, and the residue was washed with pentane. In this way the amines 4a, 4d, 5a, 6a were isolated as hydrochloride. For comparison to the reported data, the hydrochloride of 2-Tfm-pyrrolidine 8a and 2-Tfm-piperidine 8b were again treated with aqueous NaHCO3 and were analyzed as free bases.
  • 61
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  • [ 117593-76-7 ]
  • [ 532-12-7 ]
YieldReaction ConditionsOperation in experiment
77.2% Sodium hydride (17.26 g, 072 mol of 60% dispersion in a mineral oil) was washed with toluene (25 ml x 2) to remove mineral oil and added to 25 ml of DMF. To this a solution containing 1-(but-1-enyl)-pyrrolidin-2-one (I, 50 g, 0.3597 mol) and methyl nicotinate (41.8 g, 0.3057 mol) in 50 ml of DMF was added. The reaction mixture was heated to 90C for 2 hrs. DMF was partially removed under reduced pressure and 100 ml water and HCl (165 ml) were added. The reaction mixture was heated to 110C for 12 hr, cooled and washed with ethyl acetate (50 ml x 2). The aqueous layer was cooled to 0C, pH adjusted to about 14 using NaOH, extracted with dichloromethane (100 ml x 4), the extract dried over Na2SO4, the solvent removed completely and the crude solid was purified by high vacuum distillation to get myosmine (34.38 g, 77.2 % yield, 98.5% purity by GC).
  • 62
  • [ 1308392-26-8 ]
  • [ 532-12-7 ]
YieldReaction ConditionsOperation in experiment
70% A mixture of 1-(but-1-enyl)-3-nicotinoylpyrrolidin-2-one (II), (40 g, 0.1639 mol), 50 ml water and 85 ml HCl were refluxed together for 12 hrs. The reaction mixture was cooled to room temperature, washed with 50 ml x 2 ethyl acetate, further cooled to 0C and pH adjusted to >13 using NaOH. The reaction mixture was extracted with 100 ml x 3 of dichloromethane and the extract dried over Na2SO4. After removing the solvent under reduced pressure, the crude solid obtained was purified by high vacuum distillation to give colorless solid myosmine (16.75 g, 70 %). 1H NMR (CDCl3): delta 2.05 (2H, m), 2.94 (2H, t), 4.06 (2H,t), 7.34 (1H, dd), 8.18 (1H,dt), 8.64 (1H, dd), and 8.99 (1H, d). 13C-NMR(CDCl3): delta 170.56, 151.1, 149.1, 134.6, 130.0, 123.3, 61.5, 34.7, and 22.5. IR: 2961, 1620, and 1590 Cm-1.
  • 63
  • 1-(pyridin-3-yl)cyclobutane-1-carboxamide [ No CAS ]
  • [ 532-12-7 ]
  • 66
  • 3-nicotinoyl-1-vinylpyrrolidin-2-one [ No CAS ]
  • [ 532-12-7 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In tetrahydrofuran; water;Reflux; General procedure: To a solution of substituted benzoic acid 3a-h (0.07 mol) inabsolute ethyl alcohol (100 mL) was slowly added thionyl chloride (15 mL). The mixture was heated to reflux for 2 h, and then cooledto room temperature. The solvent was removed and the solid residuewas dissolved in ethyl acetate (100 mL), and washed withsaturated NaHCO3 solution (100 mL 2). The organic layer wasdried and concentrated to give the intermediates 4a-h as paleyellow oily matter in 94.4e99.4% yield. They were used in the nextstep without additional purification.To a solution of NaH (5.6 g, 0.14 mol, 60%) in anhydrous THF(250 mL) was added 4a-h (0.07 mol) under the mechanical agitation.After heating to 60 C, N-Vinylpyrrolidone (0.07 mol) wasadded by dropwise and the mixture was heated to 72 C for 3 h.Then the reaction mixture was cooled to room temperature, thenpoured into ice water (500 mL), extracted with ethyl acetate(100 3 mL), and washed with saturated NH4Cl solution (300 mL)and brine (300 mL). The organic layer was dried and concentratedto give the intermediates 5a-h as brown oily matter in 82.3e94.2%yield, which was used in the next step without additionalpurification.A solution of 5a-h (0.06 mol) in THF (15 mL) was added to the5 N HCl (60 mL) under reflux. After the reaction mixture wasrefluxed for 3e5 h, then the reaction mixture was cooled to roomtemperature and concentrated in vacuo to remove the solvent THF.The pH was adjusted to 11 with saturated NaOH solution, thenextracted with ethyl acetate (100 mL 3), and washed with brine(150 mL 2). The organic layer was dried and concentrated to givethe intermediates 6a-h as brown oily matter in 82.8e87.2% yield,which was used in the next step without additional purification.To a solution of 6a-h (0.05 mol) in methanol (80 mL) was addedacetic acid two drops, and then NaBH4 (3.8 g, 0.1mol) was addedslowly under the condition of ice salt bath. After reaction at roomtemperature for 3 h, the solvent was removed and the residue wasdissolved in water. The pH was adjusted to 1 with 6 N HCl, washedwith methyl tertiary butyl ether (50 mL 3), and then the pH wasadjusted to 12 with NaOH solution. The mixturewas extracted withdichloromethane (100 mL 3), and washed with brine(150 mL 2). The organic layer was dried and concentrated to givethe brown oil, which was dissolved in acetone to form oxalic acidsalt. Intermediates 7a-h were obtained as white solid in42.3e55.6% yield.
With hydrogenchloride; In water; at 30 - 105℃; for 3h; 1.0 eq. of ethyl nicotinate, toluene, 1.6 eq. of sodium ethoxide, and 1.2 eq. of i-vinyl-2-pyrrolidone (NVP) were charged into a flask at room temperature of about 20C under anhydrous conditions. Then the reaction was run at 100C for 3 hours. The reaction was completed, and after the mixture had been cooled down to 30C, 695.0 g HCI (36% by weight in water) was added dropwise. The low boiling components like acetaldehyde, ethanol and the gaseous CO2 were removed by distillation, together with parts of the toluene and the water. When the reaction temperature reached 105C, distillation was stopped and the reaction mixture was stirred at a temperature between 100C and 105C overnight. After completion of the reaction, the pH was adjusted to a value between 9.5 to 10.5 using NaOH (30% by weight in water). 360.0 g iso propanol and 1.0 eq. of NaBH4 (in respect of the ethyl nicotinate) were charged into the reaction vessel. The reaction was run at room temperature (about 20C) for more than 3 hours (at this point the content of myosmine was below 3.0% by weight). 2.0 eq. of formic acid (HCOOH, in respect of the ethyl nicotinate) and 1.2 eq. paraformaldehyde ((HCHO)n, in respect of the ethyl nicotinate) were added and the mixture was stirred at 65C for at least 3 hours. After the reaction was finished (at this point the content of myosmine was below 0.5% by weight), the pH of the mixture was adjusted to a value of 13 to 14 using NaOH (30% by weight in water). Water was added until all inorganic solids were dissolved. The mixture was extracted twice with toluene. The combined organic phases were concentrated to obtain the crude product. By distillation of the crude product, racemic nicotine was obtained as a colorless oil with a purity of 98.9% (yield was 66.0%) as sample 1.
With hydrogenchloride; In water; at 90 - 105℃; General procedure: The remaining reaction mixture is poured on HCI (aq., 30% in water; 58.0 g or 4.4 eq.). Low boiling components like acetaldehyde (from the?vinyl? component), ethanol and gaseous C02 were removed by distillation. When the reaction temperature reached 105C, distillation was stopped and the reaction mixture was stirred at a temperature between goC and 94C overnight. After completion of the reaction, the pH was adjusted to a value between 9.5 to 10.0 using NaOH (30% by weight in water).
  • 67
  • [ 532-12-7 ]
  • 4-[4-[2-(pyridine-3-yl)pyrrolidin-1-yl]methylphenoxyl]-1-naphthamide [ No CAS ]
  • 68
  • [ 532-12-7 ]
  • [ 59-67-6 ]
YieldReaction ConditionsOperation in experiment
84% With D-glucose; at 200℃; for 1h;pH 7.5; General procedure: Experimental procedures were performed as known in the art and important reaction details are briefly described as follows. (0061) Samples were filled in high temperature stable brown glass tubes with metal screwing. The metal cups were equipped with flexible teflon seal and placed in a special heating device in a drying oven. In all reaction experiments, 10 mM of MYO were applied which were incubated with equal amount of phosphate buffer and two fold amount of 10 mM glucose solution. Preliminary reaction assays were executed at pH values of 5, 6, and 7.5 of phosphate buffer and at different temperatures in a range of 100 to 280 C. Formation of NA was investigated at a constant reaction time with increasing temperatures and additionally at different reaction times with constant temperatures. The samples were drawn by the hour, half hour or after complete reaction time. The sample solutions were cooled to room temperature and centrifuged at 12,0000 rpm for 4 min. Aliquots of the supernatant were analyzed directly by HPLC-DAD (high pressure liquid chromatography - diode array detection) analysis. Identification of NA was performed by HPLC-DAD as known in the art in comparison with known standard solutions (co-chromatography).
  • 70
  • [ 532-12-7 ]
  • [ 25162-00-9 ]
  • 71
  • [ 532-12-7 ]
  • [ 50-00-0 ]
  • [ 22083-74-5 ]
YieldReaction ConditionsOperation in experiment
With sodium acetate; at 100℃; for 24h;Large scale; In a 10L reactor, put 1.58kg (14mol 1.5eq) of potassium tert-butoxide in sequence, N-Cbzpyrrolidone 1.85kg (8.43mol 0.9eq), and tetrahydrofuran 7.5L, after stirring for 15 minutes, 1.49 kg (9.38 mol) of methyl nicotinate in tetrahydrofuran solution 7.5 L was added dropwise to the reaction kettle. After the dropwise addition, the temperature was raised to 66 C. for reflux reaction, and the reaction time was 12 hours. After the reaction, the temperature was lowered to room temperature, and then formic acid was added dropwise at room temperature to neutralize the system to pH 7, and tetrahydrofuran was recovered to dryness by rotary evaporation under reduced pressure to obtain a first solid mixture. Subsequently, a 5L hydrochloric acid solution with a concentration of 6M was added, the temperature was raised to 100 C, and the reaction was refluxed with stirring. The reaction time was 72 hours, and the temperature was lowered to room temperature to obtain a second reaction mixture. 4kg of anhydrous sodium formate and 0.76kg of 37wt% formaldehyde were added to the second reaction mixture, stirring was continued, the temperature was raised to 100 C and the reaction was refluxed for 24 hours after the reaction, 1600 g of solid sodium hydroxide was added, bring the pH of the reaction system to 12, and extract 4 times with 5L cyclohexane, after removing the solvent, 1 kg of racemic nicotine was obtained.
  • 72
  • C18H16N2O4 [ No CAS ]
  • [ 532-12-7 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; formic acid; In water; at 100℃; for 72h;pH 7; In a 10L reactor, put 1.58kg (14mol 1.5eq) of potassium tert-butoxide in sequence, N-Cbzpyrrolidone 1.85kg (8.43mol 0.9eq), and tetrahydrofuran 7.5L, after stirring for 15 minutes, 1.49 kg (9.38 mol) of methyl nicotinate in tetrahydrofuran solution 7.5 L was added dropwise to the reaction kettle. After the dropwise addition, the temperature was raised to 66 C. for reflux reaction, and the reaction time was 12 hours. After the reaction, the temperature was lowered to room temperature, and then formic acid was added dropwise at room temperature to neutralize the system to pH 7, and tetrahydrofuran was recovered to dryness by rotary evaporation under reduced pressure to obtain a first solid mixture. Subsequently, a 5L hydrochloric acid solution with a concentration of 6M was added, the temperature was raised to 100 C, and the reaction was refluxed with stirring. The reaction time was 72 hours, and the temperature was lowered to room temperature to obtain a second reaction mixture. 4kg of anhydrous sodium formate and 0.76kg of 37wt% formaldehyde were added to the second reaction mixture, stirring was continued, the temperature was raised to 100 C and the reaction was refluxed for 24 hours after the reaction, 1600 g of solid sodium hydroxide was added, bring the pH of the reaction system to 12, and extract 4 times with 5L cyclohexane, after removing the solvent, 1 kg of racemic nicotine was obtained.
  • 73
  • [ 532-12-7 ]
  • [ 494-97-3 ]
YieldReaction ConditionsOperation in experiment
With NADPH;Enzymatic reaction; Biotransformations were undertaken at 0.5 ml_ scale with a solution of 10mM myosmine and NADP+ (0.5mM), glucose (25 mM), glucose dehydrogenase (10U/ml), and the enzyme with imine reductase activity. The enzymes used are detailed in table 1 , available from Enzymicals. For each enzyme, the amount of enzyme was 9mg/ml of cell free extract (estimated approx. 0.9mg/ml contained enzyme). For IRED_B and IRED_C specifically, additional tests were run which used 0.9 mg/ml cell free extract. The enantiomeric excess of the (S) nornicotine obtained from the biotransformation was determined using a Chiralpak AD-FI column (250 x 4.6mm id) eluting with a mixture of hexane:ethanol:diethylamine 74.9 : 25.0: 0.1 (v/v/v) at 1 ml/min over 18 min at 30 C. This method was also used to measure the conversion of myosmine into nornicotine, a relative response factor of 2.18 : 1 having been determined for uv absorption detection at 254 nm. The results are displayed in table 1 below. The % enantiomeric excess for (S)-nornicotine was identified according to the equation [(S)-(R)]/((S)+(R)] c 100 where (S) and (R) are the amounts of (S) and (R) enantiomers present respectively. The % conversion was identified according to the amount of myosmine consumed i.e. according to the equation 100- (final amount of myosmine)/(starting amount of myosmine) * 100.
  • 74
  • [ 532-12-7 ]
  • [ 494-97-3 ]
  • [ 7076-23-5 ]
YieldReaction ConditionsOperation in experiment
With NADPH;Enzymatic reaction; Biotransformations were undertaken at 0.5 ml_ scale with a solution of 10mM myosmine and NADP+ (0.5mM), glucose (25 mM), glucose dehydrogenase (10U/ml), and the enzyme with imine reductase activity. The enzymes used are detailed in table 1 , available from Enzymicals. For each enzyme, the amount of enzyme was 9mg/ml of cell free extract (estimated approx. 0.9mg/ml contained enzyme). For IRED_B and IRED_C specifically, additional tests were run which used 0.9 mg/ml cell free extract. The enantiomeric excess of the (S) nornicotine obtained from the biotransformation was determined using a Chiralpak AD-FI column (250 x 4.6mm id) eluting with a mixture of hexane:ethanol:diethylamine 74.9 : 25.0: 0.1 (v/v/v) at 1 ml/min over 18 min at 30 C. This method was also used to measure the conversion of myosmine into nornicotine, a relative response factor of 2.18 : 1 having been determined for uv absorption detection at 254 nm. The results are displayed in table 1 below. The % enantiomeric excess for (S)-nornicotine was identified according to the equation [(S)-(R)]/((S)+(R)] c 100 where (S) and (R) are the amounts of (S) and (R) enantiomers present respectively. The % conversion was identified according to the amount of myosmine consumed i.e. according to the equation 100- (final amount of myosmine)/(starting amount of myosmine) * 100.
  • 75
  • [ 532-12-7 ]
  • [ 494-97-3 ]
YieldReaction ConditionsOperation in experiment
84.7% With 10% Pd/C; hydrogen In methanol for 5h; 1.S3 S3: Synthesis of nicotine precursor, C1: Take the 3-cyclopentenylamino-pyridine obtained by taking 32 g of S2 and dissolve it in methanol, and add 1.3 g of 10% Pd/C catalyst; C2: After replacement for three times, it is filled with hydrogen with a pressure of 1 MPa. After 5 hours, excess hydrogen is released, and the reaction liquid is filtered; C3: Concentrate the filtered reaction solution to obtain 32 g of brown solid, and then distill the brown solid under reduced pressure at 0.1 mmHg to obtain 27.46 g of nicotine precursor, and the yield of nicotine precursor is 84.7%;
  • 76
  • [ 53508-48-8 ]
  • [ 532-12-7 ]
YieldReaction ConditionsOperation in experiment
1.88 kg With hydrogenchloride for 12h; Reflux; Industrial scale; 1.2-5.2 (2) The above cooling solution was slowly added to cold hydrochloric acid (12 L), and the solution was allowed to stand for liquid separation.The aqueous phase was transferred into the reaction kettle, heated under reflux for 12 hours, and the reaction process was monitored by HPLC, and the reaction was complete.After cooling to room temperature, the pH of the system was adjusted to 9.0 with liquid alkali.Extract three times with toluene.(3) Combine the toluene phases, concentrate under reduced pressure, and recover toluene.Then high vacuum distillation, the vacuum degree -0.098Mpa, obtains 1.88Kg of colorless oil, the total yield is 91.4%, and the HPLC purity is 99.2%.
  • 77
  • [ 616-45-5 ]
  • [ 10400-19-8 ]
  • [ 532-12-7 ]
YieldReaction ConditionsOperation in experiment
53.4% With triethylamine In 1,3,5-trimethyl-benzene at 80℃; Add trimethylbenzene 150g, pyrrolidone 18.5g and triethylamine 22.4g to the four-necked flask, Then 28.2g of nicotinoyl chloride was added dropwise for 1-2h. After the dropwise addition was completed, the temperature of the reaction system was raised to 80°C, and the reaction was kept for 6h. Subsequently, it was cooled to 25°C, and the insolubles (triethylamine hydrochloride) were removed by filtration to obtain a filtrate; 4.0 g of barium oxide was added to the filtrate, and then the reaction system was heated to 165 ° C, and the reaction was refluxed for 24 h. Then it was cooled to 25°C, 16g of decolorized clay was added, and finally the solvent was recovered by filtration and reduced pressure, and then 15.6g of light yellow solid was obtained by column chromatography.
  • 78
  • [ 71278-11-0 ]
  • [ 532-12-7 ]
YieldReaction ConditionsOperation in experiment
97.8% With sodium hydroxide In tetrahydrofuran; lithium hydroxide monohydrate at 40℃; Large scale; 2 Example 2: Preparation of Myosmine Add 15kg of tetrahydrofuran,5kg of water, 5kg of the compound of formula II,The temperature of the system is controlled at 40°C,1.5 kg of sodium hydroxide was added.The system was reacted at 40°C until the compound of formula II was completely consumed.The system was extracted twice with 10 kg of dichloromethane each time.The organic phases were combined and concentrated under reduced pressure at 30°C to obtain 4.35kg of myosmine,The liquid phase purity was 97.1%, and the yield: 97.8% was directly used in the next reaction.
  • 79
  • [ 9003-39-8 ]
  • [ 93-60-7 ]
  • [ 532-12-7 ]
YieldReaction ConditionsOperation in experiment
With sodium hydride In toluene; mineral oil at 60℃; Inert atmosphere; 1.1 1. Preparation of myosmine Under nitrogen protection, add 200ml of dry toluene to the reaction flask, add 14.6g of 60% NaH under stirring, stir at room temperature for 30min, add 36.8g of N-vinylpyrrolidone, and heat up to 60°C. Add 50 g of methyl nicotinate in toluene dropwise to the above reaction solution, after the dropwise addition is completed, the temperature is raised to reflux, and the reaction is carried out for 3 hours.Add 80ml of water to quench the reaction, separate the liquids, add 40ml of water to the organic phase and extract once, combine the aqueous phases, add 125ml of 36% hydrochloric acid, reflux for 3 hours, cool down, adjust the pH to 11 with 50% NaOH solution, and react at room temperature for 1 hour.Extracted with dichloromethane (200ml*2), washed once with saturated brine, dried over anhydrous sodium sulfate, and concentrated to obtain 45g of crude mesmin with a crude yield of 93%, which was directly used in the next step without purification.
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