[ CAS No. 32018-56-7 ] {[proInfo.proName]}

Name: 32018-56-7|1-Benzyl-4-methyl-1,2,3,6-tetrahydropyridine|98%
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SKU: A496638
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CAS No. :	32018-56-7	MDL No. :	MFCD09030042
Formula :	C₁₃H₁₇N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MKIZSVUTUWPHMD-UHFFFAOYSA-N
M.W :	187.28	Pubchem ID :	6421572
Synonyms :

Calculated chemistry of [ 32018-56-7 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.38
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	64.47
TPSA :	3.24 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.77 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.81
Log Po/w (XLOGP3) :	2.36
Log Po/w (WLOGP) :	2.31
Log Po/w (MLOGP) :	2.85
Log Po/w (SILICOS-IT) :	2.97
Consensus Log Po/w :	2.66

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.67
Solubility :	0.398 mg/ml ; 0.00212 mol/l
Class :	Soluble
Log S (Ali) :	-2.07
Solubility :	1.6 mg/ml ; 0.00855 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.67
Solubility :	0.0404 mg/ml ; 0.000216 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.42

Safety of [ 32018-56-7 ]

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 [ 32018-56-7 ]

* 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.

Upstream synthesis route of [ 32018-56-7 ]
Downstream synthetic route of [ 32018-56-7 ]

[ 32018-56-7 ] Synthesis Path-Upstream 1~1

1
[ 32018-56-7 ]
[ 32018-96-5 ]

Yield	Reaction Conditions	Operation in experiment
89%	With trimethylsilyl trifluoromethanesulfonate; cyclohexanone In dichloromethane at -20℃; Inert atmosphere	The starting material 1-benzyl-4-methyl-1,2,3,6-tetrahydropyridine (187 mg) was dissolved in methylene chloride(10 mL) was added. A solution of trimethylsilyl trifluorosulfonate (1.1 g) in methylene chloride was added under a nitrogen atmosphere at -20 ° C. and a catalytic amount of cyclohexanone was added. The reaction was stirred and controlled to complete the reaction. Column chromatography gave Compound II. (89percent yield).

Reference： [1] Patent: CN106831538, 2017, A, . Location in patent: Paragraph 0033; 0034
[2] Organic Process Research and Development, 2003, vol. 7, # 1, p. 115 - 120
[3] Patent: CN107337676, 2017, A,

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Yield	Reaction Conditions	Operation in experiment
98.99%	With sodium tetrahydroborate In ethanol; water at 0 - 20℃; for 12h;	48.2 Step 2: Preparation of I-Benzyl-4-methyl-3,6-dihydro-2H-pyridine: To the stirred solution of 1 -benzyl- l-bromo-4-methyl-pyridinium bromide 48-2 (56.0 g, 211.99 mmol) in a mixed solvent of EtOH (72 mL) and water (8 rnL), sodium borohydride (20 05 g, 529.98 mmol, 18.74 mL) was added portionwise at 0°C. After complete addition, the reaction mass was stirred for 12 hours at ambient temperature. After completion of the reaction as monitored by LCMS, the reaction mixture was quenched with water (30 mL) and the ethanol was removed under reduced pressure. The aqueous part was extracted with ethyl acetate (2x 200 ml). The combined organic parts were dried over anhydrous Na2S04and concentrated under vacuum. The crude residue was purified by column chromatography (100-200 silica; 2% EtOAc in hexane) to afford 1 -benzyl -4-m ethyl-3, 6- dihydro-2H-pyridine 48-3 (39.3 g, 209.85 mmol, 98.99% yield) yellow oil. LC MS: ES+ 187.8
98.99%	With sodium tetrahydroborate; ethanol In water at 0 - 20℃; for 12h;	34.2 Step 2: Synthesis of 1-benzyl-4-methyl-3,6-dihydro-2H-pyridine (3): To the stirred solution of 1-benzyl-1-bromo-4-methyl-pyridinium bromide (2) (56.0 g, 211.99 mmol) in mixed solvent of EtOH (72 mL) and Water (8 mL), Sodium borohydride (20.05 g, 529.98 mmol, 18.74 mL) was added portion wise at 0°C.After complete addition, reaction mass was stirred for 12 hr at ambient temperature.After completion of the reaction as monitored by LC MS, the reaction mixture was quenched with addition of water (30 mL) and ethanol was removed under reduced pressure.The aqueous part was extracted with ethyl acetate (2x 200 ml).The combine organic part was dried over anhydrous Na2SO4 and concentrated under vacuum.The crude residue was purified by column chromatography (100-200 silica; 2% EtOAc in Hexane) to afford 1-benzyl-4-methyl-3,6- dihydro-2H-pyridine (3) (39.3 g, 209.85 mmol, 98.99% yield) yellow oil, LC MS: ES+ 187.8.
90.1%	With methanol; potassium borohydride at -10 - -5℃; for 6h;	8; 9 2.0 g of compound II-2 was added to 20 mL of anhydrous methanol, the temperature was lowered to -5 to -10 ° C, 1.23 g of potassium borohydride was slowly added, the temperature was controlled at about -5 ° C, and after 6 hours of reaction, the solvent was evaporated to dryness, 20 mL. The organic layer was washed twice with water and dried over anhydrous sodium sulfate and evaporated.1.28 g of a brown oily liquid compound III-2 was obtained in a yield of 90.1%. The sample is designated as III-2a.

90%	With potassium borohydride In methanol at -5℃; for 4.5h;	General procedure for the reduction of pyridinium salts General procedure: All reduction reactions were run on the multi-gram scale, using the following general procedure. 1-Benzyl-4-(3-nitrophenyl)-1,2,3,6-tetrahydropyridine (1a). 17 To a solution of compound 3a (1.0 g,2.7 mmol) in MeOH (10 mL) at -5 °C was added KBH4 (0.44 g, 8.1 mmol) slowly. The resulting mixture was stirred at -5 °C for 4.5 h. The reaction was quenched with acetaldehyde solution (40% aqueous solution, 2.7 g, 24.3 mmol). The mixture was then filtered and filtrate was evaporated to dryness. The residue was extracted with CH2Cl2 (3 × 10 mL) and washed with water (30 mL). The organic layer was dried over anhydrous Na2SO4, and concentrated. The crude product was purified by column chromatography on silica gel (petroleum ether : EtOAc, 5 : 1) to provide 1a as a yellow solid (0.70 g, 89%).
90%	With tetrahydroxydiboron; potassium <i>tert</i>-butylate; water In methanol at 60℃; for 8h; Inert atmosphere;
89%	With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; triethylammonium formate; potassium iodide In dichloromethane at 40℃; for 24h; Sealed tube; chemoselective reaction;
	With sodium tetrahydroborate In ethanol Ambient temperature;
3.2 g	With sodium tetrahydroborate In methanol; water at 0 - 20℃;
27 g	With methanol; sodium tetrahydroborate at 0 - 20℃; for 1h;	19-0 A solution of Compound 19-2 (55 g, 208.2 mmol) in MeOH (100 mL) was cooled to 0° C., NaBH4 (16 g, 416.4 mmol) was added portionwise at 0° C. The reaction was stirred at room temperature for 1 hour. The reaction was concentrated in vacuo, ice H2O was added and then extracted with EtOAc (3×100 mL). The combined organic layers were washed with H2O, brine then dried over Na2SO4, filtered and concentrated in vacuo. The crude compound was purified by normal phase chromatography (40.0 g neutral alumina column) with a running gradient of 0-20% EtOAc/hexane to afford 27 g of Compound 19-3 as an oil. 1H NMR (300 MHz, CDCl3) δ 7.44-7.17 (m, 5H), 5.37 (bs, 1H), 3.57 (s, 2H), 2.98-2.90 (m, 2H), 2.56 (t, J=5.8 Hz, 2H), 2.14-2.03 (m, 2H), 1.68 (s, 3H). LC-MS=188.2 [M+H]+, retention time=0.146 minutes.

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: 1-benzyl-4-methyl-1 ,2,3,6-tetrahydropyridine With sodium tetrahydridoborate; boron trifluoride diethyl ether complex In tetrahydrofuran at 0 - 20℃; for 2.5h; Stage #2: With anhydrous potassium sulfate; sulfuric acid potassium salt; potassium peroxomonosulfate In lithium hydroxide monohydrate at 0 - 20℃;
76.2%	Stage #1: 1-benzyl-4-methyl-1 ,2,3,6-tetrahydropyridine With sodium tetrahydridoborate; boron trifluoride diethyl ether complex In tetrahydrofuran at 0℃; Stage #2: With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran; lithium hydroxide monohydrate at 50 - 60℃;	1.6 S6: Add compound 3-2 (75.29 g, 0.4 mol) and 1500 mL of tetrahydrofuran to the reaction flask respectively, add sodium borohydride (22.7 g, 0.6 mol), and slowly add boron trifluoride ether solution (111.7 mL under ice bath) , 0.8mol), at 0 °C, react for 1 to 2 hours, slowly add 320 mL of water and 52 g of sodium hydroxide, heat up to 50 to 60 °C, slowly add hydrogen peroxide (16.32 g, 0.48mol), continue the reaction 2-3 hours, followed by TLC until the reaction was complete. Cool to room temperature, adjust the pH of the reaction solution to 1, add methyl tert-butyl ether for extraction, adjust the pH of the aqueous phase to 12, add methyl tert-butyl ether for extraction, and concentrate to obtain 68.38g of a light yellow oily product, namely trans-N-benzyl-3-hydroxy-4-methylpiperidine (compound 3-3), the yield was 76.2%.

Yield	Reaction Conditions	Operation in experiment
93.2%	With sodium tetrahydridoborate In ethanol at 20℃;	1.5 S5: 4-methylpyridine (46.56g, 0.5mol), benzyl chloride (78.48g, 0.62mol), and 250mL acetonitrile were added to the reaction flask, heated to 5060, and reacted for 34 hours, followed by TLC until the reaction is complete. After the solvent was distilled off under reduced pressure, 100 mL of anhydrous ether was added, and suction filtration was performed to obtain 127.54 g of a light pink solid, 4-methylpyridine salt (compound 3-1), with a yield of 97.2%. Compound 3-1 (118.09 g, 0.45 mol) was dissolved in 500 mL of ethanol, sodium borohydride (60.53 g, 1.6 mol) was added in batches, and the reaction was carried out at room temperature for 8-10 hours, followed by TLC until the reaction was complete. After being concentrated by rotary evaporation, hydrochloric acid solution and ethyl acetate were added respectively, the aqueous phase was adjusted to pH 12 by sodium hydroxide solution, extracted with ethyl acetate, and the organic phase was concentrated to obtain 78.94g of brown oily product namely N-benzyl-4-methyl-1,2,5,6-tetrahydropyridine (compound 3-2), the yield was 93.2%.
88%	With sodium tetrahydridoborate In ethanol at 15℃; for 5h;	1.2 2. the synthesis of compound V To a 1 L reaction flask, 100 g (1.0 eq) of compound VI and 400 mL of ethanol were added, and the mixture was stirred. After cooling to 15 ° C, 20.7 g (1.2 eq) of NaBH 4In this temperature conditions, stirring 5h;TLC monitoring reaction is basically completed, then 10% diluted hydrochloric acid was added dropwise to the reaction until the pH was neutral, ethyl acetate was added to the reaction mixture was extracted twice with 200mL, the organic phases were combined, and the organic phase was washed with brine,In the external temperature 40 ~ 45 ° C conditions, concentrated to dryness under reduced pressure,The product was obtained as a yellow oil, V 75g, in 88% yield.
73%	With sodium tetrahydridoborate In ethanol at 10 - 19℃; for 17h; Inert atmosphere; Large scale;

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