10493-37-5|3-(2-Methoxyphenyl)propan-1-ol| Ambeed

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Quality Control of [ 10493-37-5 ] Purity: 95% SDS Specification

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Product Details of [ 10493-37-5 ]

CAS No. :	10493-37-5
Formula :	C₁₀H₁₄O₂
M.W :	166.22
SMILES Code :	OCCCC1=CC=CC=C1OC
MDL No. :	MFCD00197108
InChI Key :	KCJSIKPCRQDRNX-UHFFFAOYSA-N
Pubchem ID :	254958

Safety of [ 10493-37-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 10493-37-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.4
Num. rotatable bonds	4
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	48.68
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	29.46 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.21
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.32
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.62
Log P_o/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.	1.83
Log P_o/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	2.36
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.07

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.44
Solubility	0.606 mg/ml ; 0.00365 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.58
Solubility	0.44 mg/ml ; 0.00265 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	-3.16
Solubility	0.116 mg/ml ; 0.000698 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	Yes
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.	-5.67 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)	1.26

Application In Synthesis of [ 10493-37-5 ]

* 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 [ 10493-37-5 ]

[ 10493-37-5 ] Synthesis Path-Downstream 1~35

1
[ 6342-77-4 ]
[ 10493-37-5 ]

Yield	Reaction Conditions	Operation in experiment
100%		Preparation of 3-(2-methoxyphenyl)propan-l-ol3-(2-methoxyphenyl)propanoic acid (1.0 g, 5.55 mmol) was dissolved in THF (27.7 ml).A solution of borane tetrahydrofuran complex (12.21 ml, 12.21 mmol) was added slowly.The reaction was stirred for about 4 h. Methanol was added and the solvents removed.This process was repeated twice. The solution was passed through a short pad of silica gel with 1 : 1 ethyl acetate/heptane And then rotovapped to give 3-(2-methoxyphenyl)propan-l- ol (0.946 g, 5.69 mmol, 103 % yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ ppm <n="129"/>7.19 (dt, IH), 7.15 (dd, IH), 6.90 (dt, IH), 6.86 (d, IH), 3.84 (s, 3H), 3.60 (t, 2H), 2.73 (t, 2H), 1.92-1.79 (m, 2H), 1.76 (s, IH),
67%	With lithium aluminium tetrahydride; In diethyl ether; at 20℃;Reflux;	3-(2-Methoxyphenyl)propanoic acid (11.4 g, 0.0 mol) dissolved in ether (126 mL) was added slowly to a suspension of LiAlH4 (6.0 g, 0.16 mol) in ether (190 mL) at RT. The reaction was headed at reflux overnight, then cooled to RT before the reaction was quenched with water (100 mL). The reaction was filtered through a pad of celite washing with water (20 mL) and EtOAc (200 mL). The EtOAc layer was removed and the aqueous layer was extracted with more EtOAc (100 mL2). The EtOAc layers were washed with brine (100 mL) and dried (Na2SO4). Concentration gave a yellow/brown oil (5.1 g). Rewashing the celite pad with water (100 mL) and DCM (200 mL), and extracting the aqueous layer with more DCM (20 mL3) afforded more product (1.61 g). Total yield (6.71 g, 67%). 1H NMR (CDCl3, 600 MHz) δ 7.18 (1H, t, J 7.8 Hz), 7.14 (1H, d, J 6.6 Hz), 6.89 (1H, t, J 7.2 Hz), 6.85 (1H, d, J 7.8 Hz), 3.82 (3H, s), 3.60 (2H, t, J 6.0 Hz), 2.71 (2H, t, J 7.2 Hz), 1.90 (1H, bs), 1.84 (2H, t, J 6.6 Hz).
67%	With lithium aluminium tetrahydride; In diethyl ether; at 20℃;Reflux;	3-(2-Methoxyphenyl)propanoic acid (11.4 g, 0.0 mol) dissolved in ether (126 mL) was added slowly to a suspension of LiAlH4 (6.0 g, 0.16 mol) in ether (190 mL) at RT. The reaction was headed at reflux overnight, then cooled to RT before the reaction was quenched with water (100 mL). The reaction was filtered through a pad of celite washing with water (20 mL) and EtOAc (200 mL). The EtOAc layer was removed and the aqueous layer was extracted with more EtOAc (100 mL2). The EtOAc layers were washed with brine (100 mL) and dried (Na2SO4). Concentration gave a yellow/brown oil (5.1 g). Rewashing the celite pad with water (100 mL) and DCM (200 mL), and extracting the aqueous layer with more DCM (20 mL3) afforded more product (1.61 g). Total yield (6.71 g, 67%). 1H NMR (CDCl3, 600 MHz) δ 7.18 (1H, t, J 7.8 Hz), 7.14 (1H, d, J 6.6 Hz), 6.89 (1H, t, J 7.2 Hz), 6.85 (1H, d, J 7.8 Hz), 3.82 (3H, s), 3.60 (2H, t, J 6.0 Hz), 2.71 (2H, t, J 7.2 Hz), 1.90 (1H, bs), 1.84 (2H, t, J 6.6 Hz).

With lithium aluminium tetrahydride;

3-(2-Methoxyphenyl)propan-1-ol 3-(2-Methoxyphenyl)propanoic acid (11.4 g, 0.0 mol) dissolved in ether (126 mL) was added slowly to a suspension of LiAlH4 (6.0 g, 0.16 mol) in ether (190 mL) at RT. The reaction was headed at reflux overnight, then cooled to RT before the reaction was quenched with water (100 mL). The reaction was filtered through a pad of celite washing with water (20 mL) and EtOAc (200 mL). The EtOAc layer was removed and the aqueous layer was extracted with more EtOAc (100 mL*2). The EtOAc layers were washed with brine (100 mL) and dried (Na2SO4). Concentration gave a yellow/brown oil (5.1 g). Rewashing the celite pad with water (100 mL) and DCM (200 mL), and extracting the aqueous layer with more DCM (20 mL*3) afforded more product (1.61 g).

References: [1]Patent: WO2008/79382,2008,A1 .Location in patent: Page/Page column 127-128.
[2]Advanced Synthesis and Catalysis,2021,vol. 363,p. 4867 - 4875.
[3]Organic Letters,2010,vol. 12,p. 1760 - 1763.
[4]Chemistry - A European Journal,2010,vol. 16,p. 13262 - 13270.
[5]Journal of Medicinal Chemistry,2019,vol. 62,p. 7806 - 7839.
[6]Patent: US11155547,2021,B1 .Location in patent: Page/Page column 48.
[7]Patent: US11155547,2021,B1 .Location in patent: Page/Page column 48.
[8]Journal of Medicinal Chemistry,2013,vol. 56,p. 7851 - 7861.
[9]Collection of Czechoslovak Chemical Communications,1958,vol. 23,p. 1902,1907.
[10]Journal of Organic Chemistry,2004,vol. 69,p. 3610 - 3619.
[11]Journal of the Chemical Society,1939,p. 787,789.
[12]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 2771 - 2782.
[13]Bioorganic Chemistry,2018,vol. 80,p. 408 - 421.
[14]Advanced Synthesis and Catalysis,2021,vol. 363,p. 2140 - 2147.
[15]Patent: US11155547,2021,B1 .

2
[ 10493-37-5 ]
[ 38011-77-7 ]

Yield	Reaction Conditions	Operation in experiment
81%	With bromine; triphenylphosphine; In dichloromethane; at 0 - 5℃; for 4h;Cooling with ice;	3-(2-Methoxyphenyl)propan-1-ol (1.6 g, 9.7 mmol) was dissolved in DCM (43 mL) to which was added triphenylphosphine (2.7 g, 0.01 mol). The solution was cooled in an ice bath and bromine (1.6 g, 0.01 mol) was added dropwise over 4 h whilst the reaction was maintained at 0-5C. The reaction was quenched with a saturated aqueous solution of NaHCO3 (15 mL), the DCM layer removed and the aqueous layer extracted with more DCM (50 mL3). The combined organic layers were dried (Na2SO4) and concentrated to give a yellow solid. The solid was loaded onto silica (1 g) and purified by chromatography (silica, 24 g) eluting with hexane (3CV), 0-100% EtOAc in hexane (40CV) and EtOAc (CV). A clear oil was obtained (1.81 g, 81%). 1H NMR (CDCl3, 600 MHz) δ 7.19 (1H, td, J 1.8, 7.8 Hz), 7.14 (1H, dd, J 1.2, 7.2 Hz), 6.87 (1H, td, J 0.6, 7.2 Hz), 6.84 (1H, d, J 8.4 Hz), 8.31 (3H, s), 3.39 (2H, t, J 6.6 Hz), 2.75 (2H, t, J 7.2 Hz), 2.13 (2H, t, J 7.2 Hz).
81%	With bromine; triphenylphosphine; In dichloromethane; at 0 - 5℃; for 4h;Cooling with ice;	3-(2-Methoxyphenyl)propan-1-ol (1.6 g, 9.7 mmol) was dissolved in DCM (43 mL) to which was added triphenylphosphine (2.7 g, 0.01 mol). The solution was cooled in an ice bath and bromine (1.6 g, 0.01 mol) was added dropwise over 4 h whilst the reaction was maintained at 0-5C. The reaction was quenched with a saturated aqueous solution of NaHCO3 (15 mL), the DCM layer removed and the aqueous layer extracted with more DCM (50 mL3). The combined organic layers were dried (Na2SO4) and concentrated to give a yellow solid. The solid was loaded onto silica (1 g) and purified by chromatography (silica, 24 g) eluting with hexane (3CV), 0-100% EtOAc in hexane (40CV) and EtOAc (CV). A clear oil was obtained (1.81 g, 81%). 1H NMR (CDCl3, 600 MHz) δ 7.19 (1H, td, J 1.8, 7.8 Hz), 7.14 (1H, dd, J 1.2, 7.2 Hz), 6.87 (1H, td, J 0.6, 7.2 Hz), 6.84 (1H, d, J 8.4 Hz), 8.31 (3H, s), 3.39 (2H, t, J 6.6 Hz), 2.75 (2H, t, J 7.2 Hz), 2.13 (2H, t, J 7.2 Hz).
	With N-Bromosuccinimide; triphenylphosphine; In dichloromethane; at 20℃; for 16h;Ice-cooling;	(17-2) Synthesis of 1-(3-bromopropyl)-2-methoxybenzene (compound 17-2) Compound 17-1 (2.00 g) was dissolved in methylene chloride (50 ml), triphenylphosphine (3.58 g) and N-bromosuccinimide (2.40 g) were added under ice-cooling, and the mixture was stirred under ice-cooling for 1 hr, and further at room temperature for 15 hr. The reaction mixture was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. Diethyl ether (100 ml) was added, and the precipitated triphenylphosphine oxide was filtered off. The concentrate of the filtrate was purified by silica gel column chromatography (hexane alone) to give the object product (2.24 g) as a pale-brown oil. 1H-NMR(CDCl3) δ (ppm): 2.11-2.18(2H, m), 2.76(2H, t, J=7.3Hz), 3.40(2H, t, J=6.9Hz), 3.82(3H, s), 6.83-6.90(2H, m), 7.13-7.22 (2H, m).

With sodium hydrogencarbonate; triphenylphosphine;

1-(3-Bromopropyl)-2-methoxybenzene 3-(2-Methoxyphenyl)propan-1-ol (1.6 g, 9.7 mmol) was dissolved in DCM (43 mL) to which was added triphenylphosphine (2.7 g, 0.01 mol). The solution was cooled in an ice bath and bromine (1.6 g, 0.01 mol) was added dropwise over 4 h whilst the reaction was maintained at 0-5 C. The reaction was quenched with a saturated aqueous solution of NaHCO3 (15 mL), the DCM layer removed and the aqueous layer extracted with more DCM (50 mL*3). The combined organic layers were dried (Na2SO4) and concentrated to give a yellow solid. The solid was loaded onto silica (1 g) and purified by chromatography (silica, 24 g) eluting with hexane (3CV), 0-100% EtOAc in hexane (40CV) and EtOAc (CV). A clear oil was obtained (1.81 g, 81%). 1H NMR (CDCl3, 600 MHz) δ 7.19 (1H, td, J 1.8, 7.8 Hz), 7.14 (1H, dd, J 1.2, 7.2 Hz), 6.87 (1H, td, J 0.6, 7.2 Hz), 6.84 (1H, d, J 8.4 Hz), 8.31 (3H, s), 3.39 (2H, t, J 6.6 Hz), 2.75 (2H, t, J 7.2 Hz), 2.13 (2H, t, J 7.2 Hz).

References: [1]Patent: US11155547,2021,B1 .Location in patent: Page/Page column 49.
[2]Patent: US11155547,2021,B1 .Location in patent: Page/Page column 49.
[3]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1958,vol. 78,p. 183,186.
Chem.Abstr.,1958,p. 10919.
[4]Patent: EP2168944,2010,A1 .Location in patent: Page/Page column 57.
[5]Patent: US11155547,2021,B1 .

3
[ 10493-37-5 ]
[ 72734-85-1 ]

References: [1]Journal of the Chemical Society,1939,p. 787,789.
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 7851 - 7861.

4
[ 24393-54-2 ]
[ 10493-37-5 ]

References: [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1958,vol. 78,p. 183,186.
Chem.Abstr.,1958,p. 10919.
[2]Angewandte Chemie - International Edition,2017,vol. 56,p. 11807 - 11811.
Angew. Chem.,2017,vol. 129,p. 11969 - 11973.

5
[ 55001-09-7 ]
[ 10493-37-5 ]

Yield	Reaction Conditions	Operation in experiment
74.0%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 20℃; for 2.5h;	General procedure: A mixture of Lithium aluminum hydride (9.5 g, 0.250 mol), dry THF(250 mL), to it add substituted dihydrocinnamic acid methyl ester (3ae,0.127 mol), in THF (50 mL) was added slowly drop wise during30 min. After completion of addition the reaction mixture was stirredfor 2 h at rt, after completion of reaction as monitored by TLC hexane/ethyl acetate (8:2), the reaction mixture was poured in water (200 mL),acidified with 5 N HCl, extract with chloroform (2×400 mL), extractwas wash with water, brine solution, dried over Na2SO4 and concentrated.The crude residue was subjected to column chromatographyon silica gel, column was eluted with hexane/ethyl acetate mixtures,pure compound was eluted in ethyl acetate in hexane, 10%/90% (v/v)which was monitored by TLC, pure fractions were combined and concentratedto obtained 3-(substituted phenyl)- propan-1-ol as oily compoundswith yields of 73-77%.

References: [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 2771 - 2782.
[2]Bioorganic Chemistry,2018,vol. 80,p. 408 - 421.
[3]Journal of the Chemical Society,1939,p. 787,789.

6
[ 70311-27-2 ]
[ 10493-37-5 ]

References: [1]Journal of the Chemical Society,1939,p. 787,789.
[2]Chemistry Letters,2013,vol. 42,p. 1051 - 1052.
[3]Angewandte Chemie - International Edition,2017,vol. 56,p. 11807 - 11811.
Angew. Chem.,2017,vol. 129,p. 11969 - 11973.

7
[ 67563-72-8 ]
[ 10493-37-5 ]
[ 29515-39-7 ]

References: [1]Tetrahedron Letters,1993,vol. 34,p. 2343 - 2346.

8
[ 89113-48-4 ]
[ 1481-92-1 ]
[ 10493-37-5 ]

References: [1]Chemical and pharmaceutical bulletin,1983,vol. 31,p. 4178 - 4180.

9
[ 10493-37-5 ]
[ 98-59-9 ]
[ 81246-47-1 ]

References: [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 7806 - 7839.
[2]Journal of the American Chemical Society,1982,vol. 104,p. 3202 - 3209.

10
[ 1481-92-1 ]
[ 74-88-4 ]
[ 10493-37-5 ]

References: [1]Journal of the American Chemical Society,1982,vol. 104,p. 3202 - 3209.

11
[ 10493-37-5 ]
[ 33538-83-9 ]

Yield	Reaction Conditions	Operation in experiment
76.5%	With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide;	General procedure: Suitable 3-(substituted-phenyl)-propan-1-ol (4a-e, 0.02727 mol)compound was dissolved in DMSO (150 mL) and to the mixture IBX(28 g, 0.02727 mol) was added portion wise during 45 min. Aftercompletion of addition, the reaction mixture was stirred for 2 h. at roomtemperature. After completion of reaction which was monitored by TLChexane/ethyl acetate (8:2), the reaction mixture was poured into water(200 mL). The mixture was filter off; the filter bed was washed withchloroform (200 mL). The filtrate was taken in to a separating funnel,separated the organic layer and the aqueous layer was extracted withchloroform (200 mL). The combined organic layer was washed withwater, brine solution, dried over Na2SO4 and concentrated under vacuum.The crude residue was subjected to column chromatography onsilica gel, using ethyl acetate in hexane, 15%/85% (v/v) eluents asmonitored by TLC, pure fractions were combined and concentrated toobtained 3-(substituted-phenyl)-propan-1-al as oily compounds withyields of (5a-e, 73-81%).

References: [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 2771 - 2782.
[2]Bioorganic Chemistry,2018,vol. 80,p. 408 - 421.
[3]Journal of Pharmaceutical Sciences,1971,vol. 60,p. 1188 - 1192.
[4]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 2473 - 2476.
[5]Chemistry Letters,2013,vol. 42,p. 1051 - 1052.
[6]Tetrahedron Letters,2015,vol. 56,p. 1045 - 1048.
[7]Advanced Synthesis and Catalysis,2021,vol. 363,p. 2140 - 2147.

12
[ 1504-74-1 ]
[ 10493-37-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 2473 - 2476.

13
[ 6099-03-2 ]
[ 10493-37-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 2473 - 2476.
[2]Tetrahedron Letters,2015,vol. 56,p. 1045 - 1048.

14
[ 1504-61-6 ]
[ 10493-37-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 2473 - 2476.

15
[ 98288-15-4 ]
[ 10493-37-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 2473 - 2476.

16
[ 90-05-1 ]
[ 10493-37-5 ]

References: [1]Tetrahedron Letters,1993,vol. 34,p. 2343 - 2346.

17
[ 10493-37-5 ]
[ 81246-48-2 ]

References: [1]Journal of the American Chemical Society,1982,vol. 104,p. 3202 - 3209.

18
[ 10493-37-5 ]
[ 81246-42-6 ]

References: [1]Journal of the American Chemical Society,1982,vol. 104,p. 3202 - 3209.

19
[ 119-84-6 ]
sodium hydride [ No CAS ]
[ 10493-37-5 ]

References: [1]Journal of the American Chemical Society,1982,vol. 104,p. 3202 - 3209.

20
[ 10493-37-5 ]
[ 77853-46-4 ]

References: [1]Journal of the Chemical Society,1939,p. 787,789.
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 7851 - 7861.
[3]Angewandte Chemie - International Edition,2017,vol. 56,p. 11807 - 11811.
Angew. Chem.,2017,vol. 129,p. 11969 - 11973.

21
[ 135-02-4 ]
[ 10493-37-5 ]

References: [1]Collection of Czechoslovak Chemical Communications,1958,vol. 23,p. 1902,1907.
[2]Chemistry Letters,2013,vol. 42,p. 1051 - 1052.
[3]Angewandte Chemie - International Edition,2017,vol. 56,p. 11807 - 11811.
Angew. Chem.,2017,vol. 129,p. 11969 - 11973.
[4]Patent: US11155547,2021,B1 .

22
[ 10493-37-5 ]
[ 107778-98-3 ]

References: [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1958,vol. 78,p. 183,186.
Chem.Abstr.,1958,p. 10919.
[2]Patent: US11155547,2021,B1 .
[3]Patent: US11155547,2021,B1 .

23
[ 10493-37-5 ]
[ 18655-51-1 ]

24
[ 10493-37-5 ]
[ 101581-87-7 ]

25
[ 119-84-6 ]
[ 10493-37-5 ]

References: [1]Journal of Pharmaceutical Sciences,1971,vol. 60,p. 1188 - 1192.

26
2-Chloro-3-(1-piperazinyl)pyrazine.* [ No CAS ]
[ 10493-37-5 ]
[ 85386-99-8 ]
[ 313658-24-1 ]

Yield	Reaction Conditions	Operation in experiment
0.20 g (22%)	With potassium tert-butylate; In 1,4-dioxane; water; tert-butyl alcohol;	Example 211 2-[3-(2-Methoxyphenyl)propoxy]-3-(1-piperazinyl)pyrazine, Maleate A mixture of 2-chloro-3-(1-piperazinyl)pyrazine (0.40 g, 2.0 mmol; from Example 90 Step 1), 3-(2-methoxyphenyl)-propan-1-ol (0.50 g, 3.0 mmol), and KO-t-Bu (1 M in t-BuOH; 3 mL, 3 mmol) in dry dioxane (30 mL) was stirred at reflux for 20 h. The reaction was quenched by addition of water (2 mL). The solvent was evaporated and the crude mixture was passed through a column of hydromatrix material with CH2Cl2 as eluent. The elute was concentrated and the remaining oil was purified by silica gel chromatography using EtOAc/MeOH/Et3N (8:1:1) as eluent. This furnished the free base of the title compound as an oil which was converted to the maleate salt: yield 0.20 g (22%); mp 132-133 C. Anal. (C18H24N4O2.C4H4O4) C, H, N.

References: [1]Patent: US6465467,2002,B1 .

27
[ 79-37-8 ]
[ 10493-37-5 ]
[ 33538-83-9 ]

Yield	Reaction Conditions	Operation in experiment
	With dimethyl sulfoxide; triethylamine; In dichloromethane; water;	Meanwhile, a solution of 760 mg of dimethyl sulfoxide in 2 ml of methylene chloride was added dropwise to a solution of 740 mg of oxalyl chloride in 12 ml of methylene chloride at -60 C., with stirring, and the mixture was stirred at the same temperature for 10 minutes. At the end of this time, a solution of 640 mg of 3-(2-methoxyphenyl)propanol (prepared as described above) in 3 ml of methylene chloride was added dropwise to the mixture, and the mixture was stirred for a further 10 minutes. 1.96 g of triethylamine were then slowly added dropwise to the mixture at the same temperature. The cooling bath was removed, and the reaction mixture was stirred at room temperature for 30 minutes and then mixed with water. The methylene chloride layer was separated, dried over anhydrous magesium sulfate, and concentrated by evaporation under reduced pressure. The oily residue thus obtained was purified by column chromatography through silica gel, using a 5:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 540 mg of 3-(2-methoxyphenyl)propanal as a colorless oil. Nuclear Magnetic Resonance Spectrum (CDCl3, 270 MHz), δ ppm: 2.72 (2H, triplet, J=7.3 Hz); 2.95 (2H, triplet, J=7.3 Hz); 3.82 (3H, singlet); 6.8-6.95 (2H, multiplet); 7.1-7.3 (2H, multiplet); 9.80 (1H, singlet).

References: [1]Patent: US5556864,1996,A .

28
Glauber's salt [ No CAS ]
[ 24393-54-2 ]
[ 10493-37-5 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran;	PREPARATION 4 2-[4-(2-Methoxyphenyl)butyl]phenol A solution of 980 mg of ethyl 2-methoxycinnamate in 15 ml of tetrahydrofuran was added dropwise to a dispersion of 290 mg of lithium aluminum hydride and 10 ml of tetrahydrofuran, whilst ice-cooling. After the addition was complete, the reaction mixture was stirred at room temperature for 1.5 hours, and then sufficient sodium sulfate decahydrate was slowly added, whilst ice-cooling, to the mixture in order to decompose any excess of the hydride. Insoluble materials were filtered off, and the filtrate was concentrated by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 3:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 640 mg of 3-(2-methoxyphenyl)propanol as a colorless oil.

References: [1]Patent: US5556864,1996,A .

29
[ 60-29-7 ]
[ 6342-77-4 ]
[ 10493-37-5 ]

Yield	Reaction Conditions	Operation in experiment
81%	In tetrahydrofuran;	A. 2-Methoxybenzenepropanol To a solution of 3-(2-methoxyphenyl)propionic acid (2.0 g, 11.1 mmol) in tetrahydrofuran (25 mL) was added dropwise at 0 C. lithium aluminum hydride solution (1M in tetrahydrofuran, 11.1 mL, 11.1 mmol). The reaction was warmed to room temperature and stirring was continued overnight. The reaction was quenched with methanol (5 mL), and 1M potassium sodium tartrate solution (100 mL) was added. The mixture was stirred at room temperature overnight. Ethyl ether (200 mL) was added, and the organic layer was washed with water (250 mL), brine (250 mL) and dried over magnesium sulfate. Evaporation gave compound A (1.5 g, 81%) as a colorless oil.

References: [1]Patent: US5739135,1998,A .

30
[ 10493-37-5 ]
[ 124-63-0 ]
[ 146253-19-2 ]

References: [1]Organic Letters,2010,vol. 12,p. 1760 - 1763.
[2]Chemistry - A European Journal,2010,vol. 16,p. 13262 - 13270.
[3]Angewandte Chemie - International Edition,2017,vol. 56,p. 11807 - 11811.
Angew. Chem.,2017,vol. 129,p. 11969 - 11973.

31
[ 10493-37-5 ]
C₁₃H₁₅NO₃S [ No CAS ]