[ CAS No. 7583-53-1 ] {[proInfo.proName]}

Name: 7583-53-1|1-Methyl-3-piperidinemethanol|97%
Brand: Ambeed
SKU: A103093
Price: 10.0 USD
Availability: InStock
Rating: 93 (40 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 7583-53-1 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 7583-53-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 7583-53-1 ]

SDS Specification

Alternatived Products of [ 7583-53-1 ]

Product Details of [ 7583-53-1 ]

CAS No. :	7583-53-1	MDL No. :	MFCD00006497
Formula :	C₇H₁₅NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UGXQXVDTGJCQHR-UHFFFAOYSA-N
M.W :	129.20	Pubchem ID :	97998
Synonyms :

Calculated chemistry of [ 7583-53-1 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	41.62
TPSA :	23.47 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.86 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.93
Log Po/w (XLOGP3) :	0.32
Log Po/w (WLOGP) :	-0.06
Log Po/w (MLOGP) :	0.57
Log Po/w (SILICOS-IT) :	0.78
Consensus Log Po/w :	0.71

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.78
Solubility :	21.6 mg/ml ; 0.167 mol/l
Class :	Very soluble
Log S (Ali) :	-0.38
Solubility :	54.3 mg/ml ; 0.421 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.55
Solubility :	36.2 mg/ml ; 0.28 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.64

Safety of [ 7583-53-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H227-H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 7583-53-1 ]

* 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 [ 7583-53-1 ]
Downstream synthetic route of [ 7583-53-1 ]

[ 7583-53-1 ] Synthesis Path-Upstream 1~4

1
[ 1690-72-8 ]
[ 7583-53-1 ]

Reference： [1] Patent: WO2016/144844, 2016, A1, . Location in patent: Page/Page column 35

2
[ 4606-65-9 ]
[ 7583-53-1 ]

Reference： [1] Patent: US5827881, 1998, A,

3
[ 498-95-3 ]
[ 7583-53-1 ]

Reference： [1] Patent: WO2016/144844, 2016, A1,

4
[ 50585-89-2 ]
[ 7583-53-1 ]

Reference： [1] Patent: WO2016/144844, 2016, A1,

[ 7583-53-1 ] Synthesis Path-Downstream 1~88

1
[ 7583-53-1 ]
[ 40052-13-9 ]
[ 127945-26-0 ]

Reference： [1]Liebigs Annalen der Chemie,1990,p. 975 - 988

2
[ 7583-53-1 ]
[ 30293-86-8 ]
[ 147146-13-2 ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 320 - 330

3
[ 7583-53-1 ]
[ 110521-96-5 ]
[ 128014-59-5 ]

Reference： [1]Archiv der Pharmazie,1990,vol. 323,p. 9 - 12

4
[ 7583-53-1 ]
[ 100415-25-6 ]
[ 127944-76-7 ]

Reference： [1]Liebigs Annalen der Chemie,1990,p. 975 - 988

5
[ 7583-53-1 ]
[ 151-50-8 ]
[ 132462-26-1 ]
[ 132462-26-1 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 2386 - 2390
[2]Journal of Organic Chemistry,1991,vol. 56,p. 2386 - 2390

6
[ 7583-53-1 ]
[ 98-88-4 ]
[ 132462-24-9 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 2386 - 2390

7
[ 7583-53-1 ]
[ 137364-92-2 ]
C₁₇H₂₈N₃O₂⁽¹⁺⁾*H⁽¹⁺⁾ [ No CAS ]
C₁₇H₂₈N₃O₂⁽¹⁺⁾*H⁽¹⁺⁾ [ No CAS ]

Reference： [1]Angewandte Chemie,1991,vol. 103,p. 1690 - 1692

8
[ 7583-53-1 ]
[ 77042-85-4 ]
[ 77042-70-7 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 1877 - 1888

9
[ 7583-53-1 ]
[ 4122-68-3 ]
[ 80842-08-6 ]

Reference： [1]European Journal of Medicinal Chemistry,1985,vol. 20,p. 559 - 562

10
[ 7583-53-1 ]
[ 74-88-4 ]
[ 131297-57-9 ]

Reference： [1]Journal of Physical Chemistry,1990,vol. 94,p. 8885 - 8890

11
[ 7583-53-1 ]
[ 66496-82-0 ]

Reference： [1]European Journal of Medicinal Chemistry,1994,vol. 29,p. 967 - 974

12
[ 7583-53-1 ]
3-[4-(2-piperidin-1-yl-ethoxy)-benzyl]-2-(4-triisopropylsilanyloxy-phenyl)-benzo[b]thiophen-6-ol [ No CAS ]
2-(4-(N-methylpiperidino-3-methyloxy)-phenyl)-3-(4'-(2-piperidinoethyloxy)phenyl)-6-hydroxybenzothiophene [ No CAS ]

Reference： [1]Tetrahedron,1999,vol. 55,p. 11641 - 11652

14
[ 7583-53-1 ]
[ 849200-12-0 ]
(2,6-dimethyl-phenyl)-{5-[3-(1-methyl-piperidin-3-ylmethoxy)-phenyl]-imidazo[1,5-a]pyrazin-8-yl}-amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 868 - 885

15
[ 7583-53-1 ]
[ 849200-11-9 ]
(2,6-dimethyl-phenyl)-{5-[4-(1-methyl-piperidin-3-ylmethoxy)-phenyl]-imidazo[1,5-a]pyrazin-8-yl}-amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 868 - 885

16
[ 7583-53-1 ]
[ 98-59-9 ]
[ 94759-32-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	With dmap; triethylamine; In dichloromethane; at 20℃; for 2h;	Toluene-4-sulfonic acid 1-methyl-piperidin-3-ylmethyl ester A mixture of 2.07 g (16 mmol) 1-methyl-3-piperidinemethanol, 3.35 g (18 mmol) p-toluensulfonyl chloride, 0.58 g (5 mmol) 4-dimethylaminopyridine and 2.23 mL (16 mmol) NEt3 in 30 mL DCM was stirred for 2 h at room temperature. The mixture was washed with water and evaporated to dryness to yield 4.5 g (99%) of the title compound as yellow oil which was used without further purification. MS(m/e): 284.1 (MH+).
58%	With triethylamine; In dichloromethane; at 0 - 20℃; for 6h;	To a stirred solution of 1 -methyl-3 -hydroxymethylpiperidine (2 g, 15.5 mmol) in DCM (30 mL) at 0C, triethylamine (4.9 g, 46 mmol) and tosyl chloride (4.41 g, 23.2 mmol) were added and allowed the mixture to stir at room temperature for 6 h. After completion, the reaction mixture was diluted with water (30 mL) and extracted with DCM (3 x 30 mL). The combined organic layer was dried over sodium sulfate and concentrated. The resulting crude was purified by flash chromatography (silica gel, 12 g cartridge) using 0-20% EtOAc in hexanes as eluent to obtain (l-methylpiperidin-3-yl)methyl 4- methylbenzenesulfonate (Yield: 2.50 g, 58%) as white solid. LCMS (ES) m/z = 284.36 [M+H]+; NMR (400 MHz, DMSO-d6) d ppm: 0.87-0.95 (m, 1H), 1.33-1.50 (m, 4H), 1.63 (m, 1H), 1.80-1.85 (m, 2H), 2.06 (s, 3H), 2.42 (s, 3H), 2.46-2.52 (m, 1H), 3.90 (m, 2H), 7.48 (d, J= 8.0 Hz, 2H). 7.78 (d, J= 8.0 Hz, 2H).
	With dmap; In dichloromethane; at 20℃; for 12h;Cooling with ice;	10.0 g of 1-methyl-3-piperidinemethanol are dissolved in 100 ml of dichloromethane, and 9.46 g of 4-dimethylaminopyridine and 15.5 g of p-toluenesulfonyl chloride are added with ice cooling The reaction solution is stirred at room temperature for twelve hours and then washed with saturated NaHCO3 solution and dried over MgSO4, and the solvent is removed under reduced pressure. The resulting residue is dissolved in 150 ml of acetone, and 39.5 g of sodium iodide are added. The reaction mixture is heated at the boil under reflux for two hours. The solvent is then removed under reduced pressure, and the residue is taken up in 300 ml of ethyl acetate and washed twice with in each case 100 ml of water. The organic phase is dried over MgSO4 and then concentrated under reduced pressure. This gives 9.4 g of 3-iodomethyl-1-methylpiperidine. C7H141N (239.10), LCMS (ESI): 240.0 (M+H+).

With triethylamine; In dichloromethane; at 20℃; for 5h;

Into a 250 mL round bottom flask containing a solution of (l-methylpiperidin-3- yl)methanol (8.0 g, 62 mmol) in dichloromethane (80 mL) was added triethylamine (17 mL, 125 mmol) followed by the addition of p-toluenesulfonyl chloride (14.2 g, 75 mmol) and the reaction mixture stirred at room temperature for 5 h. The reaction mixture was diluted with dichloromethane and washed with water and brine solution. The organic fraction was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude was purified by flash chromatography eluting with methanol in dichloromethane (5-7%) to afford (1-methylpiperidin-3-yl)methyl 4-methylbenzenesulfonate as a liquid. 1H NMR (DMSO-d6; 400 MHz): delta 7.80 (d, J = 7.8 Hz, 2H), 7.11 (d, J = 7.8 Hz, 2H), 4.01-3.91 (m, 2H), 3.21-3.16 (m, 2H), 2.64-2.58 (m, 2H), 2.43 (s, 3H), 2.42-2.29 (m, 1H), 2.09 (s, 3H), 1.77-1.74 (m, 2H), 1.62- 1.59 (m, 2H). MS calc'd [M+H]+ 284.1, found 284.4.

Reference： [1]Patent: US2007/270423,2007,A1 .Location in patent: Page/Page column 14
[2]Patent: WO2019/175897,2019,A1 .Location in patent: Paragraph 00098
[3]Journal of Medicinal Chemistry,2019,vol. 62,p. 7210 - 7232
[4]Patent: US2009/325942,2009,A1 .Location in patent: Page/Page column 41
[5]Patent: WO2016/144844,2016,A1 .Location in patent: Page/Page column 35-36

17
[ 7583-53-1 ]
[ 337308-68-6 ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 1785 - 1788

18
[ 7583-53-1 ]
Benzaldehyde O-(1-methyl-piperidin-3-ylmethyl)-oxime [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1994,vol. 29,p. 967 - 974

19
[ 7583-53-1 ]
2,4-Dimethyl-pentan-3-one O-(1-methyl-piperidin-3-ylmethyl)-oxime [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1994,vol. 29,p. 967 - 974

20
[ 7583-53-1 ]
Pyridine-3-carbaldehyde O-(1-methyl-piperidin-3-ylmethyl)-oxime [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1994,vol. 29,p. 967 - 974

21
[ 7583-53-1 ]
Bicyclo[2.2.1]heptan-2-one O-(1-methyl-piperidin-3-ylmethyl)-oxime [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1994,vol. 29,p. 967 - 974

22
[ 7583-53-1 ]
1-Phenyl-ethanone O-(1-methyl-piperidin-3-ylmethyl)-oxime [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1994,vol. 29,p. 967 - 974

23
[ 7583-53-1 ]
Diphenyl-methanone O-(1-methyl-piperidin-3-ylmethyl)-oxime [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1994,vol. 29,p. 967 - 974

24
[ 7583-53-1 ]
Benzo[1,3]dioxole-5-carbaldehyde O-(1-methyl-piperidin-3-ylmethyl)-oxime [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1994,vol. 29,p. 967 - 974

25
[ 7583-53-1 ]
Fluoren-9-one O-(1-methyl-piperidin-3-ylmethyl)-oxime [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1994,vol. 29,p. 967 - 974

26
[ 7583-53-1 ]
[ 1026875-67-1 ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 320 - 330

27
[ 7583-53-1 ]
{(S)-1-[(1S,2R,3S)-1-Benzyl-3-((S)-2-benzyloxycarbonylamino-3-methyl-butyrylamino)-2-hydroxy-4-phenyl-butylcarbamoyl]-2-methyl-propyl}-carbamic acid 1-methyl-piperidin-3-ylmethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 320 - 330

28
[ 7583-53-1 ]
[ 132462-27-2 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 2386 - 2390
[2]Journal of Organic Chemistry,1991,vol. 56,p. 2386 - 2390

29
[ 7583-53-1 ]
[ 132462-27-2 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 2386 - 2390
[2]Journal of Organic Chemistry,1991,vol. 56,p. 2386 - 2390

30
[ 7583-53-1 ]
[ 127945-27-1 ]

Reference： [1]Liebigs Annalen der Chemie,1990,p. 975 - 988

31
[ 7583-53-1 ]
[ 127945-29-3 ]

Reference： [1]Liebigs Annalen der Chemie,1990,p. 975 - 988

32
[ 7583-53-1 ]
[ 127945-28-2 ]

Reference： [1]Liebigs Annalen der Chemie,1990,p. 975 - 988

33
[ 7583-53-1 ]
[ 127971-18-0 ]

Reference： [1]Liebigs Annalen der Chemie,1990,p. 975 - 988

34
[ 7583-53-1 ]
[ 124-63-0 ]
[ 1312785-99-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine; In dichloromethane; at 20℃; for 2h;	Into a 100-mL round-bottom flask, was placed (l-methylpiperidin-3- yl)methanol (1 g, 7.74 mmol, 1 equiv), dichloromethane (20 mL), TEA (2.349 g, 23.21 mmol, 3.00 equiv), MsCl (1.326 g, 11.63 mmol, 1.50 equiv). The resulting solution was stirred for 2 h at 20 °C. The resulting mixture was concentrated under vacuum. This resulted in 1.6 g (100percent) of the title compound as a yellow solid.
	In dichloromethane; at 0 - 20℃; for 24h;	3-HYDROXYMETHYL-L-METHYLPIPERIDINE (2 g, 9.66 mmol) was dissolved in DCM (15 mL), the solution was cooled to 0 °C and METHANESULFONYL chloride (0.9 mL, 11.6 mmol) was added dropwise. The reaction was then allowed to warm up to room temperature and left stirring for 24 H. After this time water (20 mL) was added to the reaction and the organic layer was separated, dried over NA2S04, filtered and solvent removed to give a colourless OIL. 1H NMR indicated a mixture of the starting piperidine and the desired product. This was then dissolved in acetonitrile (30 ML) along with 2-FLUORO-4-NITROPHENOL (1.52 g. , 9.66 mmol); potassium carbonate (2.67 g. , 19.32 mmol) was added and the reaction was heated at 90 °C for 18 h, then allowed to cool to room temperature. The solids were filtered and solvent removed from the filtrate. This gave 3.5 g of an orange oil. Column chromatography (5percent MeOH/DCM) gave a yellow solid which was shown to be a mixture of 2-fluoro-4-nitrophenol and 3- (2-FLUORO-4-NITROPHENOXYMETHYL)-L- methylpiperidine. The material was partitioned between DCM (30 mL) and saturated potassium carbonate solution (30 mL). The DCM layer was removed and washed with 5M HC1 (20 mL). The acidic layer was then basified to pH 10 and extracted twice with DCM (30 mL). The organics combined, dried over NA2SO4, filtered and solvent removed to give 3-(2-FLUORO-4-NIKOPHENOXYMETHYL)-1- methylpiperidine as a yellow OIL. 1NMR (400 MHz, (CD30D) 8.16-8. 06 (2 H, M), 7.33 (1 H, T, J8. 8), 4.17 (1 H, M), 4.09 (1 H, M), 3.32 (1 H, D, J 10. 8), 3.02 (1 H, t, J 11.5), 2.47 (3 H, s), 2.22 (3 H, M), 1. 89 (3 H, M), 1.75 (1 H, M), 1.28 (1 H, M).
	In dichloromethane; at 20℃; for 24h;	General Scheme J; General Method J; Preparation of 3- (2-Fluoro-4-nitrophenoxymethyl)-1-methylpiperidine; 3-Hydroxymethyl-l-methylpiperidine (2 g, 9.66 mmol) was dissolved in DCM (15 mL), the solution was cooled to 0 °C and methanesulfonyl chloride (0.9 mL, 11.6 mmol) was added dropwise. The reaction was then allowed to warm up to room temperature and left stirring for 24 h. After this time water (20 mL) was added to the reaction and the organic layer was separated, dried over Na2S04, filtered and solvent removed to give a colorless oil. 1H NMR indicated a mixture of the starting piperidine and the desired product. This was then dissolved in acetonitrile (30 mL) along with 2-fluoro-4-nitrophenol (1.52 g. , 9.66 mmol) ; potassium carbonate (2.67 g. , 19.32 mmol) was added and the reaction was heated at 90 °C for 18 h, then allowed to cool to room temperature. The solids were filtered and solvent removed from the filtrate. This gave 3.5 g of an orange oil. Column chromatography (5percent MeOH/DCM) gave a yellow solid which was shown to be a mixture of 2-fluoro-4-nitrophenol and 3-(2-fluoro-4-nitrophenoxymethyl)-1- methylpiperidine. The material was partitioned between DCM (30 mL) and saturated potassium carbonate solution (30 mL). The DCM layer was removed and washed with 5M HC1 (20 mL). The acidic layer was then basified to pH 10 and extracted twice with DCM (30 mL). The organics combined, dried over Na2SO4, filtered and solvent removed to give 3-(2-fluoro-4-nitrophenoxymethyl)-1- methylpiperidine as a yellow oil. 1NMR (400 MHz, (CD30D) 8.16-8. 06 (2 H, m), 7. 33 (1 H, t, J8. 8), 4.17 (1 H, m), 4.09 (1 H, m), 3. 32 (1 H, d, J 10. 8), 3.02 (1 H, t, J 11.5), 2.47 (3 H, s), 2.22 (3 H, m), 1. 89 (3 H, m), 1.75 (1 H, m), 1. 28 (1 H, m).; Alternatively, the nitro derivative was prepared as follows: 3,4-Difluoronitro phenol (3 g, 18. 7 mmol) and 3-hydroxy-1-methylpiperidine (2.5 g, 19.3 mmol) were dissolved in dry THF (100 mL) under nitrogen. Sodium hydride (60percent, 1 g, 25 mmol) was slowly added under positive nitrogen pressure. The resulting light yellow solution was heated at 60 °C for 2.5 h. The dark-red solution was left to cool to room temperature and quenched with a solution of acetic acid (0.3 mL, 5.2 mmol) in methanol (10 mL). Solvent was removed under reduced pressure to yield an orange solid that was purified by column chromatography using DCM: MeOH (75: 25) as eluent to yield 3- (2-fluoro-4-nitro phenoxymethyl)-l- methylpiperidine as an orange oil.

0.65 g

With triethylamine; In dichloromethane; at 0 - 20℃; for 5h;

Step a. To a stirred solution of (l-methylpiperidin-3-yl)methanol (CAS Number 7583-53-1; available from Ark Pharm) (0.5 g, 3.876 mmol) in DCM (10 ml) was added TEA (0.78 g, 7.752 mmol) and methane sulfonyl chloride (0.66 g, 5.804 mmol) at 0°C. The reaction mixture was stirred at rt for 5 h. The reaction mixture was poured into water (20 ml) and saturated NaHC03 solution (10 ml) and extracted with EtOAc (3 x 50 ml). The combined organic phase was washed with brine solution (20 ml), dried over Na2S04, filtered and concentrated under reduced pressure. The resulting residue was purified by flash chromatography (5percent MeOH in DCM) yielding (1-methylpiperidin-3-yl)methyl methanesulfonate (0.65 g, 3.136 mmol); NMR (400 MHz, DMSO-d6) delta ppm 4.04 - 4.13 (m, 2 H), 3.17 (s, 3 H), 2.68 (d, J=8.8 Hz, 1H), 2.57 (d, J=10.4 Hz, 1H), 2.15 (s, 3 H), 1.87 - 1.92 (m, 2 H), 1.76 (t, J=10 Hz, 1H), 1.59 - 1.63 (m, 2 H), 1.41 - 1.50 (m, 1H), 0.97 - 1.05 (m, 1H).

Reference： [1]Patent: WO2017/181177,2017,A1 .Location in patent: Paragraph 01051-01053
[2]Patent: WO2005/9978,2005,A1 .Location in patent: Page 68-69
[3]Patent: WO2005/42518,2005,A2 .Location in patent: Page/Page column 68-69
[4]Organic and Biomolecular Chemistry,2010,vol. 8,p. 2164 - 2173
[5]Patent: WO2017/158388,2017,A1 .Location in patent: Page/Page column 93

35
[ 7583-53-1 ]
[ 403-19-0 ]
[ 837421-40-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; In tetrahydrofuran; at 60℃; for 2.5h;Product distribution / selectivity;	General Scheme J; General Method J; Preparation of 3- (2-Fluoro-4-nitrophenoxymethyl)-1-methylpiperidine; 3-Hydroxymethyl-l-methylpiperidine (2 g, 9.66 mmol) was dissolved in DCM (15 mL), the solution was cooled to 0 °C and methanesulfonyl chloride (0.9 mL, 11.6 mmol) was added dropwise. The reaction was then allowed to warm up to room temperature and left stirring for 24 h. After this time water (20 mL) was added to the reaction and the organic layer was separated, dried over Na2S04, filtered and solvent removed to give a colorless oil. 1H NMR indicated a mixture of the starting piperidine and the desired product. This was then dissolved in acetonitrile (30 mL) along with 2-fluoro-4-nitrophenol (1.52 g. , 9.66 mmol) ; potassium carbonate (2.67 g. , 19.32 mmol) was added and the reaction was heated at 90 °C for 18 h, then allowed to cool to room temperature. The solids were filtered and solvent removed from the filtrate. This gave 3.5 g of an orange oil. Column chromatography (5percent MeOH/DCM) gave a yellow solid which was shown to be a mixture of 2-fluoro-4-nitrophenol and 3-(2-fluoro-4-nitrophenoxymethyl)-1- methylpiperidine. The material was partitioned between DCM (30 mL) and saturated potassium carbonate solution (30 mL). The DCM layer was removed and washed with 5M HC1 (20 mL). The acidic layer was then basified to pH 10 and extracted twice with DCM (30 mL). The organics combined, dried over Na2SO4, filtered and solvent removed to give 3-(2-fluoro-4-nitrophenoxymethyl)-1- methylpiperidine as a yellow oil. 1NMR (400 MHz, (CD30D) 8.16-8. 06 (2 H, m), 7. 33 (1 H, t, J8. 8), 4.17 (1 H, m), 4.09 (1 H, m), 3. 32 (1 H, d, J 10. 8), 3.02 (1 H, t, J 11.5), 2.47 (3 H, s), 2.22 (3 H, m), 1. 89 (3 H, m), 1.75 (1 H, m), 1. 28 (1 H, m).; Alternatively, the nitro derivative was prepared as follows: 3,4-Difluoronitro phenol (3 g, 18. 7 mmol) and 3-hydroxy-1-methylpiperidine (2.5 g, 19.3 mmol) were dissolved in dry THF (100 mL) under nitrogen. Sodium hydride (60percent, 1 g, 25 mmol) was slowly added under positive nitrogen pressure. The resulting light yellow solution was heated at 60 °C for 2.5 h. The dark-red solution was left to cool to room temperature and quenched with a solution of acetic acid (0.3 mL, 5.2 mmol) in methanol (10 mL). Solvent was removed under reduced pressure to yield an orange solid that was purified by column chromatography using DCM: MeOH (75: 25) as eluent to yield 3- (2-fluoro-4-nitro phenoxymethyl)-l- methylpiperidine as an orange oil.

Reference： [1]Patent: WO2005/42518,2005,A2 .Location in patent: Page/Page column 68-69

36
[ 7583-53-1 ]
[ 41886-04-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With pyridine; dibromotriphenylphosphorane; In acetonitrile; at 0 - 25℃; for 94h;	3-(HYDROXYMETHYL)-1-METHYLPIPERIDINE (2g, 15. 5MMOLES) was dissolved in anhydrous acetonitrile (32mL) and anhydrous pyridine (2.02mL, 24. 8mmoles) was added and the solution was cooled to 0 C. Dibromotriphenylphosphorane (8. 49G, 20. 2mmoles) was added at 0 C and the mixture was allowed to warm up to 25 C and was stirred for 94h. The mixture was evaporated to dryness and the residue was chromatographed on a silica gel column (30x5cm) using gradient elution with dichloromethane, 35percent diethyl ether in DICHLOROMETHANE and 5-10percent methanol in dichloromethane as the eluant to give 3-(BROMOMETHYL)-1- METHYLPIPERIDINE (3.13g, 100percent): FABMS: m/z 192.1 (MH+) ; 8H (CDCI3) 1.52 (1H, m, CH2), 1. 99 (2H, m, CH2), 2.43 (1 H, m, CH2), 2.75 (2H, m, CH2), 2.82 (1 H, m, CH), 2.86/2. 88 (3H, s, NCH3), 3.42/3. 49 (2H, dd,-CH2Br) and 3.56 ppm (2H, m, CH2); 8C (CDCI3) CH3 : 44.3 ; CH2: 22.1, 26.6, 35.4, 54.8, 58.2 ; CH: 34. 6.

Reference： [1]Patent: WO2004/22561,2004,A1 .Location in patent: Page 108

37
[ 7583-53-1 ]
[ 193001-79-5 ]
[ 263400-84-6 ]

Yield	Reaction Conditions	Operation in experiment
	With triphenylphosphine; diethylazodicarboxylate; In methanol; dichloromethane;	4-(4-Chloro-2-fluorophenoxy)-7-hydroxy-6-methoxyquinazoline (12.1g, 38mmol), (prepared as described for the starting material in Example 5), was suspended in dichloromethane (375ml) and treated with triphenylphosphine (29.6g, 113mmol) then stirred at ambient temperature for 30 minutes. (1-Methylpiperidin-3-yl)methanol (8.25g, 63.8mmol) and (R)-(1-methylpiperidin-3-yl)methanol (1.46g, 11.3mmol), (CAS 205194-11-2), giving R:S (57.5:42.5 by chiral HPLC) (9.7g, 75mmol) were dissolved in dichloromethane (75ml) and added to the suspension. Diethyl azodicarboxylate (17.7ml, 75mmol) was added in portions using a syringe pump and the mixture was then allowed to warm to ambient temperature and stirred overnight. The residue was concentrated under vacuum then chromatographed on silica eluding with dichloromethane followed by dichloromethane/methanol /ammonia (93/6/1). The relevant fractions were combined and evaporated to give an oil. The residue was triturated with ether, filtered and dried to give (R,S)-4-(4-chloro-2-fluorophenoxy)-6-methoxy-7-((1-methylpiperidin-3-yl)methoxy)quinazoline (8.7g, 53percent). 1H NMR Spectrum: (DMSOd6) 1.11(m, 1H); 1.50(m, 1H); 1.58-1.98(m, 4H); 2.09(m, 1H); 2.15(s, 3H); 2.62(d, 1H); 2.81(d, 1H); 3.95(s, 3H); 4.09(d, 2H); 7.39(m, 2H); 7.55(m, 2H); 7.67(d, 1H); 8.53(s, 1H) MS (ESI): 432 (MH)+

Reference： [1]Patent: EP1154774,2005,B1 .Location in patent: Page/Page column 51

38
[ 7583-53-1 ]
[ 288383-91-5 ]
4-(2,3-dimethylindol-5-yloxy)-6-methoxy-7-(1-methylpiperidin-3-ylmethoxy)quinazoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		j) 4-(2,3-Dimethylindol-5-yloxy)-7-hydroxy-6-methoxyquinazoline (97 mg) was reacted with 1-methyl-3-piperidinemethanol (75 mg) to give 4-(2,3-dimethylindol-5-yloxy)-6-methoxy-7-(1-methylpiperidin-3-ylmethoxy)quinazoline.

Reference： [1]Patent: EP1154774,2005,B1 .Location in patent: Page/Page column 85

39
[ 7583-53-1 ]
[ 7693-52-9 ]
3-(4-bromo-2-nitro-phenoxymethyl)-1-methyl-piperidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; for 12h;	To a stirred solution of 1-methylpiper-idine-3-methanol (1 g, 5.3 mmol), 2-nitro-4-bromo-phenol (1.15 g, 5.3 mmol), and triphenylphosphine(1.39 g, 5.3 mmol) in dry THF (25 mL) under a nitro- gen atmosphere was added dropwise a solution ofdiisopropyl azodicarboxylate (1.04 mL, 5.3 mmol).The resulting mixture was stirred at room tempera- ture for 12 hours, then was diluted with ethylacetate (75 mL) and washed with brine (2 x 50 mL).The combined organic layers were dried over MgS04,filtered, and concentrated under reduced pressure.The crude material was purified on columnchromatography (silica gel) and eluted with 5percent MeOHin CH2C12 to yield a colorless oil.

Reference： [1]Patent: WO2006/12308,2006,A1 .Location in patent: Page/Page column 56

40
[ 7583-53-1 ]
[ 446-36-6 ]
[ 457099-08-0 ]

Yield	Reaction Conditions	Operation in experiment
		1-[4-Fluoro-2-(1-methyl-piperidin-3-ylmethoxy)-phenyl]-3-(5-methyl-pyrazin-2-yl)-urea Prepared according to the methods for compound 303, using 2-nitro-5-fluorophenol and 1-methyl-3-hydroxymethyl piperidine. 1H NMR (400 MHz, CDCl3) delta8.50 (br s, 1H), 8.19 (m, 2H), 6.65 (m, 2H), 3.85 (m, 2H), 3.60 (s, 3H), 2.80-3.20 (m, 2H), 2.54 (s, 3H), 2.39 (s, 3H), 1.60-2.10 (m 5H). LRMS (ESI, Positive) m/e 373.95 (M+1).

Reference： [1]Patent: US2003/69284,2003,A1

41
[ 7583-53-1 ]
[ 364-74-9 ]
[ 457099-05-7 ]

Yield	Reaction Conditions	Operation in experiment
		1-[5-Fluoro-2-(1-methyl-piperidin-3-ylmethoxy)-phenyl]-3-(5-methyl-pyrazin-2-yl)-urea Steps 1-2: According to procedure for compound 300, using 1,4-difluoro-2-nitrobenzene and 1-methyl-3-hydroxymethyl piperidine.

Reference： [1]Patent: US2003/69284,2003,A1

42
[ 7583-53-1 ]
[ 94759-32-7 ]

Yield	Reaction Conditions	Operation in experiment
85%	With triethylamine; In dichloromethane;	Step A Toluene-4-sulfonic acid 1-methyl-piperidin-3-ylmethyl Ester (1-Methyl-piperidin-3-yl)-methanol (1.0 mL, 7.75 mmol, 1 eq) was suspended in dry CH2Cl2 (20 mL) under Ar. Triethylamine (1.9 mL, 14 mmol, 2.0 eq) was added followed by thc addition of toluencsulfonyl chloride (1.49 g, 7.8 mmol, 1.0 eq.). The reaction mixture was stirred at room temperature for 18 hours, and then quenched with aqueous sodium bicarbonate. The aqueous layers were extracted several times with CH2Cl2, and the combined organic layers were dried over Na2SO4. After removing the solvent, the residue was loaded on silica gel and chromatographed (ethyl acetate/methanol/triethylamine 87/10/3). 1.85 g (85percent yield) of the amine tosylate was obtained as a yellow oil.

Reference： [1]Patent: US2003/64991,2003,A1

43
[ 7583-53-1 ]
ethereal hydrogen chloride [ No CAS ]
[ 10465-81-3 ]
[ 193001-59-1 ]
[ 205193-45-9 ]

Yield	Reaction Conditions	Operation in experiment
33%	With tributylphosphine; In dichloromethane; acetone;	Alternatively the racemate may be made as follows: 1,1'-(Azodicarbonyl)dipiperidine (560 mg, 2.2 mmol) was added in portions to a mixture of 4-(4-chloro-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline (240 mg, 0.75 mmol), (prepared as described for the starting material in Example 2), 1-methyl-3-piperidinemethanol (115 mg, 0.89 mmol) and tributylphosphine (440 mg, 2.2 mmol) in methylene chloride (10 ml). The mixture was stirred for 18 hours, diluted with ether and the resulting precipitate was removed by filtration. The volatiles were removed from the filtrate by evaporation, and the residue was dissolved in acetone and ethereal hydrogen chloride (1.5 ml of a 1M solution, 1.5 mmol) was added. The precipitated product was collected by filtration and purified by column chromatography eluding with methylene chloride/methanol/aqueous ammonia (75/8/1). The purified solid product was triturated with ether collected by filtration and dried to give 4-(4chloro-2-fluoroanilino)-6-methoxy-7-(1-methylpiperidin-3-ylmethoxy)quinazoline (105 mg, 33percent). m.p. 211-212° C.; 1H NMR Spectrum: (DMSOd6) 1.08(m, 1H); 1.50(m, 1H); 1.78(m, 4H); 2.08(m, 1H); 2.16(m, 3H); 2.62(m, 1H); 2.82(m, 1H); 3.95(s, 3H); 4.00(d, 2H); 7.18(s, 1H); 7.32(m, 1H); 7.52(dd, 1H); 7.58(t, 1H); 7.79(s, 1H); 8.35(s, 1H); 9.52(s, 1H); MS-ESI: 431 [MH]+; Elemental analysis: Found C, 59.9; H, 5.5; N, 12.9; C22H24N4O2ClF 0.5H2O Requires C, 60.0; H, 5.7; N, 12.7percent.

Reference： [1]Patent: US6414148,2002,B1

44
[ 7583-53-1 ]
[ 1336-21-6 ]
[ 193001-79-5 ]
[ 1972-28-7 ]
[ 263400-84-6 ]

Yield	Reaction Conditions	Operation in experiment
53%	With triphenylphosphine; In methanol; dichloromethane;	A mixture of 4-(4-chloro-2-fluorophenoxy)-7-hydroxy-6-methoxyquinazoline (12.1 g), triphenylphosphine (29.6 g) and methylene chloride (375 ml) was stirred at ambient temperature for 30 minutes. The reaction mixture was cooled in an ice-bath and a solution of N-methylpiperidin-3-ylmethanol (8.25 g) in methylene chloride (75 ml) was added followed by the portionwise addition of diethyl azodicarboxylate (17.7 ml). The reaction mixture was allowed to warm to ambient temperature and was stirred overnight. The mixture was concentrated under vacuum and the residue was purified by column chromatography on silica using initially methylene chloride and then a 93:6:1 mixture of methylene chloride, methanol and an aqueous ammonium hydroxide solution as eluent. The material so obtained was triturated under diethyl ether. There was thus obtained 4-(4-chloro-2-fluorophenoxy)-6-methoxy-7-(N-methylpiperidin-3-ylmethoxy)quinazoline (8.7 g, 53percent); NMR: (DMSOd6) 1.11 (m, 1H), 1.5 (m, 1H), 1.58-1.98 (m, 4H), 2.09 (m, 1H), 2.15 (s, 3H), 2.62 (d, 1H), 2.81 (d, 1H), 3.95 (s, 3H), 4.09 (d, 2H), 7.39 (m, 2H), 7.55 (m, 2H), 7.67 (d, 1H), 8.53 (s, 1H); Mass: M+H+ 432.

Reference： [1]Patent: US6593333,2003,B1

45
[ 7583-53-1 ]
[ 2374-05-2 ]
[ 1972-28-7 ]
3-(4-bromo-2,6-dimethylphenoxymethyl)-1-methylpiperidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With ammonium hydroxide; triphenylphosphine; In tetrahydrofuran; dichloromethane;	A. Preparation of I where R1, R2 and R6 are Methyl, R3 and R5 are Hydrogen, and R4 is Bromo 3-Hydroxymethyl-1-methylpiperidine (0.4 mL, 3.14 mmol) and triphenylphosphine (1.01 g, 3.85 mmol) were added to a solution of 4-bromo-2,6-dimethylphenol (517 mg, 2.57 mmol) in tetrahydrofuran (10 mL) at 0° C. under dry nitrogen, followed by the dropwise addition of diethyl azodicarboxylate (0.57 mL, 3.60 mmol). The mixture was stirred at 0° C. for 4 hours and the solvent removed in vacuo. The residue was purified on silica gel, eluding with 5percent methanol in dichloromethane containing 0.25percent ammonium hydroxide, to give 3-(4-bromo-2,6-dimethylphenoxymethyl)-1-methylpiperidine as an oil (531 mg, 66percent).

Reference： [1]Patent: US6110937,2000,A

46
[ 7583-53-1 ]
[ 4620-67-1 ]
[ 202736-61-6 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 58 (1-Methyl-3-piperidino)methyl 1-phenylcyclobutanecarboxylate Hydrochloride The title compound was prepared in an analogous manner to that in Example 36 by reacting 1-phenylcyclobutanecarbonyl chloride with 1-methyl-3-piperidinemethanol at 80° C. for 18 h. The yield was 1.4 g (77percent); mp 126-128° C.; 1 H NMR (D2 O) delta 1.15 (m, 1H), 1.67-1.81 (m, 2H), 1.97 (m, 2H), 2.05-2.19 (m, 2H), 2.42 (t, 1H), 2.64 (m, 2H), 2.73 (m, 1H), 2.80 (s, 3H), 2.87 (m, 2H), 3.17 (d, 1H), 3.49 (d, 1H), 4.09 (q, 1H), 4.17 (q, 1H), 7.44 (t, 1H), 7.49 (d, 2H), 7.54 (t, 2H). Anal. (C18 H25 NO2.HCl) C, H, N.

Reference： [1]Patent: US6124354,2000,A

47
[ 4606-65-9 ]
[ 7583-53-1 ]

Yield	Reaction Conditions	Operation in experiment
76%	With sodium hydroxide; formaldehyd; formic acid;	EXAMPLE 5 [(N-Methyl-3-piperidyl)methyl]-[trans-2'-(N,N-dibutylamino)cyclohexyl] carbonate hydrochloride hydrate A! At 0° C., 3-hydroxymethyl-piperidine (20 g, 173 mmoles) was slowly added to formic acid (63 ml, 1.66 moles) then a 40percent solution of formaldehyde was added (62.4 ml, 833 mmoles). The mixture was refluxed for 5 hours, then the solvent was evaporated and the residue taken up in little water, brought to basic pH with 32percent sodium hydroxide and extracted with ethyl ether. The organic phase was anhydrified over sodium sulfate and evaporated. The resultant crude was purified by distillation and provided 17 g (yield: 76percent) of N-methyl-3-hydroxymethylpiperidine (b.p.--85°-86° C./1 mmHg).

Reference： [1]Patent: US5827881,1998,A

48
[ 7583-53-1 ]
[ 881842-49-5 ]
[ 881842-52-0 ]

Yield	Reaction Conditions	Operation in experiment
40%	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20℃; for 3h;	To a stirred solution of compound II (3 mg, 0.009 mmol) in THF (1.0 mL) was added (l-methylpiperidin-3-yl)methanol (5.0 muL, 0.036 mmol), triphenylphosphine (16 mg, 0.048 mmol) and diethyl azodicarboxylate (6.3 muL, 0.048 mmol). After stirring at room temperature for 3 h, the reaction mixture was concentrated. The residue was dissolved in THF/water (3:2, 0.8 mL), passed through a 0.45 mum filter, and purified by HPLC on a Varian Inertsil.(R). 5mu ODS-3 (250x100) reverse-phase HPLC column. Elution with 10percent to 90percent gradient of 0.1percent EPO <DP n="83"/>AcOH in water/0.1 percent AcOH in CH3CN over 40 min provided IV (1.7 mg, 40percent yield): LRMS m/z (M+H) calcd for C25H34NO8 476.2; obsd 476.2.

Reference： [1]Patent: WO2006/36941,2006,A2 .Location in patent: Page/Page column 80; 81

49
[ 7583-53-1 ]
1,1-Dimethyl-3-hydroxymethylpiperidinium p-toluenesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		REFERENCE EXAMPLE 5 1,1-Dimethyl-3-hydroxymethylpiperidinium p-toluenesulfonate The procedures of Reference Example 3 were repeated using 2.58 g of 1-methyl-3-piperidinemethanol and 3.72 g of methyl p-toluenesolfonate, to give 5.13 g of the desired compound, m.p. 130°-132° C. 1 H NMR (DMSO-d6) delta: 0.8-2.1 (m, 5H), 2.29 (s, 3H), 2.6-3.6 (m, 6H), 3.03 (s, 3H), 3.11 (s, 3H), 4.79 (t, 1H), 6.9-7.6 (m, 4H). IR (KBr) cm-1: 3360, 3050, 3020, 2940, 2910, 2860, 1480, 1450, 1215, 1190, 1045, 1010, 820, 700, 560.

Reference： [1]Patent: US4962096,1990,A

50
[ 7583-53-1 ]
[ 75-09-2 ]
[ 52694-50-5 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride;	Preparation 1F Following a procedure similar to that described in Preparation 1D above, a solution of 95 g. (0.735 mole) of 3-hydroxymethyl-1-methylpiperidine in 600 ml. of MDC was cooled to 0° C. and treated dropwise with 53.6 ml. of thionyl chloride. When addition was complete, the reaction mixture was heated to reflux for one hour and then taken to dryness to give 135 g. of 3-chloromethyl-1-methylpiperidine.

Reference： [1]Patent: US5068234,1991,A

51
[ 7583-53-1 ]
[ 1034-39-5 ]
[ 41886-04-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With pyridine; In methanol; dichloromethane; acetonitrile;	A. 3-(BROMOMETHYL)-1-METHYLPIPERIDINE <strong>[7583-53-1]3-(Hydroxymethyl)-1-methylpiperidine</strong> (2 g, 15.5 mmoles) was dissolved in anhydrous acetonitrile (32 mL) and anhydrous pyridine (2.02 mL, 24.8 mmoles) was added and the solution was cooled to 0° C. Dibromotriphenylphosphorane (8.49 g, 20.2 mmoles) was added at 0° C. and the mixture was allowed to warm up to 25° C. and was stirred for 94 h. The mixture was evaporated to dryness and the residue was chromatographed on a silica gel column (30*5 cm) using gradient elution with dichloromethane, 35percent diethyl ether in dichloromethane and 5-10percent methanol in dichloromethane as the eluant to give 3-(bromomethyl)-1-methylpiperidine (3.13 g, 100percent): FABMS: m/z 192.1 (MH+); deltaH (CDCl3) 1.52 (1H, m, CH2), 1.99 (2H, m, CH2), 2.43 (1H, m, CH2), 2.75 (2H, m, CH2), 2.82 (1H, m CH), 2.86/2.88 (3H, s, NCH3), 3.42/3.49 (2H, dd, -CH2Br) and 3.56 ppm (2H, m, CH2); deltaC (CDCl3) CH3: 44.3; CH2: 22.1, 26.6, 35.4, 54.8, 58.2; CH: 34.6.

Reference： [1]Patent: US2004/209878,2004,A1

52
[ 7583-53-1 ]
[ 2622-89-1 ]
[ 207730-19-6 ]

Reference： [1]Journal of Organometallic Chemistry,1998,vol. 553,p. 221 - 239

53
[ 7583-53-1 ]
[ 75-24-1 ]
dimethylaluminium (+);(-)-N-methyl-3-piperidyloxide [ No CAS ]

Reference： [1]Zeitschrift fur Anorganische und Allgemeine Chemie,1998,vol. 624,p. 315 - 321

54
[ 7583-53-1 ]
[ 943772-98-3 ]
[ 76-05-1 ]
{4-[4-(4-bromo-phenylcarbamoyl)-2-(7-isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-phenylsulfanyl]-phenyl}-carbamic acid 1-methyl-piperidin-3-ylmethyl ester trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%		Example 159; {4-[4-(4-Bromo-phenylcarbamoyl)-2-(7-isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)- phenylsulfanyl]-phenyl}-carbamic acid l-methyl-piperidin-3-ylmethyl ester; [05861 The product from Example 100 (76 mg, 0.1 mmol), (l-methyl-piperidin-3-yl)-methanol (65 mg, 0.5 mmol) and l ,8-diazabicyclo[5.4.0]undec-7-ene (15 muL, 0.1 mmol) in tetrahydrofuran (5 <n="162"/>mL) was heated at 60 0C for 1 hour. The mixture was added saturated sodium carbonate, extracted with ethyl acetate, dried with magnesium sulfate, filtered and evaporated. The residue was purified by reverse phase preparative HPLC with TFA method to give the title compound as a trifluoroacetic acid salt (36 mg, 37percent). 1H NMR (300 MHz, DMSOd6) delta ppm:. 1.20 (m, 1 H) 1.36 (d, J=6.99 Hz3 6 H) 1.78 (m, 3 H) 2.14 (m, 1 H) 2.79 (d, J=4.04 Hz, 3 H) 3.28 (m, 1 H) 3.44 (m, 4 H) 4.02 (m, 2 H) 7.07 (d, J=8.09 Hz, 1 H) 7.40 (d, J=8.82 Hz, 2 H) 7.54 (m, 4 H) 7.73 (d, J=8.82 Hz, 2 H) 7.85 (m, 2 H) 7.98 (s, 1 H) 8.79 (s, 1 H) 8.95 (d, J=8.46 Hz, 1 H) 9.46 (s, 1 H) 9.96 (s, 1 H) 10.38 (s, 1 H) 11.38 (s, 1 H); MS (ESI+) m/z 740 742 (M+H)+.
37%		The product from Example 60 (76 mg, 0.1 mmol), (l-methyl-piperidin-3-yl)- methanol (65 mg, 0.5 mmol) and l,8-diazabicyclo[5.4.0]undec-7-ene (15 muL, 0.1 mmol) in tetrahydrofuran (5 mL) was heated at 60 0C for 1 hour. The mixture was added saturated sodium carbonate, extracted with ethyl acetate, dried with magnesium sulfate, filtered and evaporated. The residue was purified by reverse phase preparative HPLC with TFA method to give the title compound as a trifluoroacetic acid salt (36 mg, 37percent). 1H NMR (300 MHz, DMSO-d6) delta ppm: 1.20 (m, 1 H) 1.36 (d, J=6.99 Hz, 6 H) 1.78 (m, 3 H) 2.14 (m, 1 H) 2.79 (d, J=4.04 Hz, 3 H) 3.28 (m, 1 H) 3.44 (m, 4 H) 4.02 (m, 2 H) 7.07 (d, J=8.09 Hz, 1 H) 7.40 (d, J=8.82 Hz, 2 H) 7.54 (m, 4 H) 7.73 (d, J=8.82 Hz, 2 H) 7.85 (m, 2 H) 7.98 (s, 1 H) 8.79 (s, 1 H) 8.95 (d, J=8.46 Hz, 1 H) 9.46 (s, 1 H) 9.96 (s, 1 H) 10.38 (s, 1 H) 11.38 (s, 1 H); MS (ESI+) m/z 740 742 (M+H)+.

Reference： [1]Patent: WO2007/76034,2007,A2 .Location in patent: Page/Page column 160-161
[2]Patent: WO2008/133753,2008,A2 .Location in patent: Page/Page column 118

55
[ 7583-53-1 ]
[ 1897-52-5 ]
[ 872180-57-9 ]

Yield	Reaction Conditions	Operation in experiment
		Example 20; 5-(1-Methylpiperidin-3-ylmethoxy)quinazoline-2,4-diamine; [0093] Step 1; Sodium hydride (60percent; 316 mg; 7.9 mmol) was suspended in DMF and cooled to 0 °C. 1-Methylpiperdin-3-ylmethanol (998 mg; 7.5 mmol) was added dropwise to the sodium hydride mixture. The solution was allowed to warm to room temperature and stirred for 30 minutes. The solution was then cooled to 0 °C. 2,6- Difluorobenzonitrile (1.1 g; 7.9 mmol) in DMF was cooled to 0° C and the alcohol mixture was added dropwise to the benzonitrile solution and allowed to warm to room temperature overnight. The solution was poured into water and extracted with dichloromethane and solvent removed. Purification by column chromatography (10percent ethyl acetate/ hexane) to yield 79 milligrams of 2-fluoro-6-(1-methylpiperidin-3- ylmethoxy) benzonitrile.

Reference： [1]Patent: WO2005/123724,2005,A1 .Location in patent: Page/Page column 30

56
[ 7583-53-1 ]
[ 1417646-31-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 552 - 557

57
[ 7583-53-1 ]
[ 1417646-43-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 552 - 557

58
[ 7583-53-1 ]
C₁₇H₂₂N₂O₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 552 - 557

59
[ 7583-53-1 ]
[ 223718-30-7 ]
[ 1417646-24-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 552 - 557

60
[ 7583-53-1 ]
2-hydroxy-5-([methyl(phenyl)amino]-carbonyl}oxy)benzoic acid [ No CAS ]
C₂₂H₂₆N₂O₅ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 3757 - 3766

61
[ 7583-53-1 ]
[ 111-82-0 ]
(3-lauroyloxymethyl-1-methylpiperidinium-1-yl)acetate [ No CAS ]

Reference： [1]Patent: WO2016/64620,2016,A1

62
[ 7583-53-1 ]
[ 111-82-0 ]
(1-methylpiperidin-3-yl)methyl laurate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
401.7 g	With Novozym 435; In n-heptane; at 65℃; under 65 - 85 Torr;Dean-Stark;	To a 3-neck, 2-L round bottom flask fitted with an overhead stirrer and a Dean-Stark trap with cold-finger condenser was added methyl laurate (302 g, 1 .41 mol) and 3-hydroxymethyl-1 -methylpiperidine (200 g, 1 .56 mol). Novozym 435 (30 g) was added, followed by the addition of heptane (120 mL). The internal pressure was reduced to 85 mm Hg and controlled by a vacuum regulator. The mixture was heated to 65°C. After 1 .5 hrs, 23 ml_ of methanol had collected in the Dean-Stark trap. At that point, the reaction was cooled to ambient temperature. The mixture was allowed to stand overnight. The following morning, the pressure was once again reduced to 85 mm Hg, and the mixture was heated to 65°C. The reaction was checked by 1 H NMR after 5.5 hours. Additional 3-hydroxymethyl-1 -methylpiperidine (9.00 g) was added. After 7.5 hrs, the mixture was cooled to ambient temperature. Then additional 3-hydroxymethyl-4-methylpiperidine (17.9 g) was once again added. The pressure was reduced to 65 mm Hg, and the mixture was heated to 65°C. After 5 hrs, the reaction was stopped. The mixture was filtered, and the solids were washed with additional heptane. Heptane (500 ml_) was added to the organics, which were then washed with water (1 x 500 ml_). After the layers were separated, the organics were dried with Na2SO4. After filtration, most of the volatiles were removed at reduced pressure. The remaining material was heated to 50°C and sparged (subsurface) for ca. 24 hrs with nitrogen at 100 mL/min to drive off residual heptane affording the title compound as a pale yellow oil (401 .7 g) that was 98.4percent pure by 1 H NMR analysis. 1 H NMR (300 MHz, CDCI3) delta 3.95 (m, 2H), 2.08 (m, 2H), 2.30 (t, J = 9 Hz, 2H), 2.27 (s, 3H) 2.01 -1 .83 (m, 2H); 1 .77-1 .56 (m, 8H); 1 .37-1 .21 (m, 17H), 0.89 (t, 3H).HPLC (150 x 4.6 mm Zorbax SB-C8 column, 75:25 (v:v) (0191) methanol :water (containing 0.1 vol percent trifluoroacetic acid) for 10 min, gradient to 100percent methanol over 1 min, held at 100percent methanol for 9 min, ELSD detection): tR (laurate ester) 5.0 min.

Reference： [1]Patent: WO2016/64620,2016,A1 .Location in patent: Paragraph 0085

63
[ 7583-53-1 ]
[ 32315-10-9 ]
(7R,9Z)-18-hydroxyoctacos-9-en-7-yl acetate [ No CAS ]
(7R,9Z)-18-([(1-methylpiperidin-3-yl)methoxy]carbonyl}oxy)octacos-9-en-7-yl acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
110 mg		A solution of the mixture containing (7R,9Z)-18-hydroxyoctacos-9-en-7-yl acetate (0.33 g) obtained in Reference Example 48 and pyridine (0.35 g, 4.5 mmol) in toluene (7.1 mL) was cooled to 0°C in an ice bath, and a solution of triphosgene (0.14 g, 0.49 mmol) in toluene (1.1 mL) was added thereto over 1 minute. After stirring at 0°C for 10 minutes, the reaction mixture was heated to room temperature, stirred for 30 minutes, and cooled to 0°C again. (1-Methyl-3-piperidyl)methanol (0.96 g, 7.4 mmol) was added thereto, and the mixture was reacted at room temperature for 90 minutes. After treatment with a saturated aqueous solution of sodium bicarbonate, the reaction mixture was subjected to extraction with ethyl acetate, and the obtained organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was then subjected to silica gel column chromatography to obtain the compound of interest as a colorless liquid (110 mg). 1H-NMR (400 MHz, CDCl3) delta: 0.86 - 0.91 (6H, m), 0. 93-1.05 (1H, m), 1.17 - 1.38 (36H, m), 1.48 - 1.78 (8H, m), 1.85 - 1.94 (1H, m), 1.96 - 2.07 (6H, m), 2.24 - 2.34 (5H, m), 2.74 (1H, d, J = 10.5 Hz), 2.86 (1H, d, J = 10.5 Hz), 3.95 (1H, ddd, J = 2.7, 7.4, 10.2 Hz), 4.06 (1H, ddd, J = 2.7, 5.9, 10.2 Hz), 4.64 - 4.71 (1H, m), 4.87 (1H, quint, J = 6.3 Hz), 5.27 - 5.37 (1H, m), 5.43 - 5.51 (1H, m). MS (ESI+) m/z 622 [M+H]+ HRMS (ESI+) m/z 622.5438 (2.8 mDa).

Reference： [1]Patent: EP3020701,2016,A1 .Location in patent: Paragraph 0406

64
[ 7583-53-1 ]
[ 32315-10-9 ]
(6Z,9Z,26Z,29Z)-pentatriaconta-6,9,26,29-tetraen-18-ol [ No CAS ]
(1-methylpiperidin-3-yl)methyl (6Z,9Z,26Z,29Z)-pentatriaconta-6,9,26,29-tetraen-18-yl carbonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%		A solution of (6Z,9Z,26Z,29Z)-pentatriaconta-6,9,26,29-tetraen-18-ol (0.22 g, 0.44 mmol) obtained in Reference Example 4 and pyridine (0.22 g, 2.8 mmol) in toluene (4.4 mL) was cooled to 0°C in an ice bath, and a solution of triphosgene (0.090 g, 0.30 mmol) in toluene (0.66 mL) was added thereto over 2 minutes. After stirring at 0°C for 15 minutes, the reaction mixture was heated to room temperature, stirred for 1 hour, and cooled to 0°C again. (1-Methyl-3-piperidyl)methanol (0.60 g, 4.6 mmol) was added thereto, and the mixture was reacted overnight at room temperature. After treatment with a saturated aqueous solution of sodium bicarbonate, the reaction mixture was subjected to extraction with ethyl acetate-hexane, and the obtained organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was then subjected to silica gel column chromatography to obtain the compound of interest as a colorless liquid (201 mg, 70percent). 1H-NMR (400 MHz, CDCl3) delta: 0.89 (6H, m), 0.92 - 1.04 (1H, m), 1.21 - 1.40 (36H, m), 1.48 - 1.78 (8H, m), 1.85 - 1.94 (1H, m), 1.96 - 2.10 (9H, m), 2.26 (3H, s), 2.77 (4H, t, J = 6.6 Hz), 2.72 - 2.90 (2H, m), 3.94 (1H, dd, J = 7.4, 10.6 Hz), 4.05 (1H, dd, J = 5.5, 10.6 Hz), 4.64 - 4.72 (1H, m), 5.28 - 5.42 (8H, m). MS (ESI+) m/z 656 [M+H]+ HRMS (ESI+) m/z 656.5981 (-0.1 mDa).

Reference： [1]Patent: EP3020701,2016,A1 .Location in patent: Paragraph 0402

65
[ 7583-53-1 ]
[ 32315-10-9 ]
[ 809272-96-6 ]
(1-methylpiperidin-3-yl)methyl triacontan-11-yl carbonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%		To a solution of triacontan-11-ol (0.18 g, 0.41 mmol) obtained in Reference Example 63 and pyridine (0.20 g, 2.6 mmol) in toluene (4.1 mL), a solution of triphosgene (0.084 g, 0.28 mmol) in toluene (0.62 mL) was added over 2 minutes. After stirring at room temperature for 1 hour, 1-methyl-3-piperidinemethanol (0.56 g, 4.3 mmol) was added thereto, and the mixture was reacted overnight at room temperature. After treatment with a saturated aqueous solution of sodium bicarbonate, the reaction mixture was subjected to extraction with hexane, and the obtained organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was then subjected to silica gel column chromatography to obtain the compound of interest as a colorless liquid (145 mg, 60percent). 1H-NMR (400 MHz, CDCl3) delta: 0.89 (6H, t, J = 7.0 Hz), 1.20 - 1.36 (50H, m), 1.48 - 1.77 (8H, m), 1.85 - 1.94 (1H, m), 1.95 - 2.07 (1H, m), 2.26 (3H, s), 2.75 (1H, d, J = 10.9 Hz), 2.86 (1H, d, J = 10.9 Hz), 3.94 (1H, dd, J = 7.4, 10.9 Hz), 4.06 (1H, dd, J = 5.9, 10.9 Hz), 4.64 - 4.71 (1H, m). MS (ESI+) m/z 594 [M+H]+ HRMS (ESI+) m/z 594.5827 (0.2 mDa).

Reference： [1]Patent: EP3020701,2016,A1 .Location in patent: Paragraph 0429

66
[ 7583-53-1 ]
[ 32315-10-9 ]
(19Z,22Z)-octacosa-19,22-dien-11-ol [ No CAS ]
(1-methylpiperidin-3-yl)methyl (9Z,12Z)-octacosa-19,22-dien-11-yl carbonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%		A solution of (19Z,22Z)-octacosa-19,22-dien-11-ol (0.26 g, 0.64 mmol) obtained in Reference Example 17 and pyridine (0.32 g, 4.0 mmol) in toluene (7.4 mL) was cooled to 0°C in an ice bath, and a solution of triphosgene (0.13 g, 0.44 mmol) in toluene (0.9 mL) was added thereto over 2 minutes. After stirring at 0°C for 20 minutes, the reaction mixture was heated to room temperature, stirred for 1 hour, and cooled to 0°C again. (1-Methyl-3-piperidyl)methanol (0.87 g, 6.7 mmol) was added thereto, and the mixture was reacted overnight at room temperature. After treatment with a saturated aqueous solution of sodium bicarbonate, the reaction mixture was subjected to extraction with hexane, and the obtained organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was then subjected to silica gel column chromatography to obtain the compound of interest as a colorless liquid (360 mg, 55percent). 1H-NMR (500 MHz, CDCl3) delta: 0.85 - 0.91 (6H, m), 1.21-1.39 (32H, m), 1.49 - 1.76 (9H, m), 1.86 - 1.92 (1H, m), 1.96 - 2.07 (5H, m), 2.26 (3H, s), 2.74 (1H, d, J = 10.5 Hz), 2.77 (2H, t, J = 6.8 Hz), 2.85 (1H, d, J = 10.5 Hz), 3.94 (1H, dt, J = 3.2, 7.3 Hz), 4.06 (1H, ddd, J = 3.2, 5.9, 10.7 Hz), 4.65 - 4.71 (1H, m), 5.29 - 5.42 (4H, m). MS (ESI+) m/z 562 [M+H]+ HRMS (ESI+) m/z 562.5196 (-0.3 mDa).

Reference： [1]Patent: EP3020701,2016,A1 .Location in patent: Paragraph 0306

67
[ 50585-89-2 ]
[ 7583-53-1 ]

Reference： [1]Patent: WO2016/144844,2016,A1

68
[ 1690-72-8 ]
[ 7583-53-1 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 1h;	Into a 500 mL round bottom flask containing a solution of methyl 1-methylpiperidine-3- carboxylate (12.0 g, 76 mmol) in tetrahydrofuran (500 mL) was added lithium aluminumhydride (4.3 g, 114 mmol) in portions at 0 °C and the reaction mixture was stirred at room temperature for 1 h. The reaction was quenched with methanol at 0 °C and the precipitated solid was filterred through celite. The filtrate was concentrated and the crude was purified by flash chromatography eluting with methanol in dichloromethane (5-10percent) to afford (1-methylpiperidin-3-yl)methanol as a solid. 1H NMR (DMSO-d6, 400 MHz): delta 3.38-3.35 (m, 1H), 3.27-3.20 (m, 1H), 3.18-3.15 (m, 1H), 2.77-2.72 (m, 1H), 2.66-2.60 (m, 2H), 2.10 (s, 3H), 1.78-1.75 (m, 1H), 1.73-1.51 (m, 4H), 1.48-1.29 (m, 1H). MS calc'd [M+H]+ 130.1, found 130.2.

Reference： [1]Patent: WO2016/144844,2016,A1 .Location in patent: Page/Page column 35

69
[ 7583-53-1 ]
[ 1042152-71-5 ]

Reference： [1]Patent: WO2016/144844,2016,A1

70
[ 7583-53-1 ]
methyl 1-((1-methylpiperidine-3-yl)methyl)-4-nitro-1H-pyrazole-3-carboxylate [ No CAS ]

Reference： [1]Patent: WO2016/144844,2016,A1

71
[ 7583-53-1 ]
1-((1-methylpiperidin-3-yl)methyl)-4-nitro-1H-pyrazole-3-carboxamide [ No CAS ]

Reference： [1]Patent: WO2016/144844,2016,A1

72
[ 7583-53-1 ]
4-amino-1-((1-methylpiperidin-3-yl)methyl)-1H-pyrazole-3-carboxamide [ No CAS ]

Reference： [1]Patent: WO2016/144844,2016,A1

73
[ 7583-53-1 ]
tert-butyl 6-(((1-methylpiperidin-3-yl)methyl)amino)-4-phenylisoindoline-2-carboxylate [ No CAS ]

Reference： [1]Patent: WO2017/158388,2017,A1

74
[ 7583-53-1 ]
N-((1-methylpiperidin-3-yl)methyl)-7-phenylisoindolin-5-amine hydrochloride [ No CAS ]

Reference： [1]Patent: WO2017/158388,2017,A1

75
[ 7583-53-1 ]
6-(((1-methylpiperidin-3-yl)methyl)amino)-4-phenylisoindoline-2-carbonitrile [ No CAS ]

Reference： [1]Patent: WO2017/158388,2017,A1

76
[ 7583-53-1 ]
3-(2-methoxy-5-nitrophenoxymethyl)-1-methylpiperidine [ No CAS ]

Reference： [1]Patent: WO2017/181177,2017,A1

77
[ 7583-53-1 ]
4-methoxy-3-[(1-methylpiperidin-3-yl)methoxy]aniline [ No CAS ]

Reference： [1]Patent: WO2017/181177,2017,A1

78
[ 7583-53-1 ]
N2-(4-methoxy-3-((1-methylpiperidin-3-yl)methoxy)phenyl)-N4-methylpyrimidine-2,4-diamine [ No CAS ]

Reference： [1]Patent: WO2017/181177,2017,A1

79
[ 7583-53-1 ]
N2-(4-methoxy-3-((1-methylpiperidin-3-yl)methoxy)phenyl)-N4,6-dimethylpyrimidine-2,4-diamine [ No CAS ]

Reference： [1]Patent: WO2017/181177,2017,A1

80
[ 7583-53-1 ]
[ 34334-96-8 ]
C₁₁H₁₈N₄O₂ [ No CAS ]
C₁₁H₁₈N₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22%; 23%	With cyanomethylenetributyl-phosphorane; In toluene; at 50℃; for 18h;Sealed tube;	General procedure: The reaction was performed in 2 batches. In a sealed tube, cyanomethylenetributyl phosphorane (9.28 mL, 35.40 mmol) was added to a solution of 3-methyl-5-nitro-lH- pyrazole (1.50 g, 1 1.80 mmol) and 3-hydroxymethyl-3-methyloxethane (3.53 mL, 35.40 mmol) in toluene (100 mL). The solution was heated at 60 °C for 18 h. The 2 batches were combined and the solvent was evaporated in vacuo. The residue (black oil) was purified by column chromatography on silica gel (irregular SiOH, 15-40 muiotaeta, 330 g, liquid loading on DCM, mobile phase: heptane/EtOAc, gradient from 90: 10 to 50:50). The fractions containing the product were combined and evaporated to dryness to give 3.95 g of intermediate 303 (79percent yield, orange oil) directly used as it in the next step.

Reference： [1]Patent: WO2018/2217,2018,A1 .Location in patent: Page/Page column 299; 302

81
[ 7583-53-1 ]
C₁₂H₉FN₂O [ No CAS ]
1-(3-(5-((1-methylpiperidin-4-yl)methoxy)pyrimidin-2-yl)phenyl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%		Sodium hydride (60percent, 1.5 mmol) was added portionwise to 1-methylpiperidine-3-methanol (1.2 mmol) at 0 °C.In 10 mL of N,N-dimethylformamide solution,Stir for 15 minutes,Intermediate 2 was then slowly added to the mixture at 0 ° C.The reaction mixture was slowly warmed to room temperature and stirred for 1 hour.The reaction solution was diluted with water.Extracted with ethyl acetate,Drying the combined organic layers,Rotary evaporation to give the crude product.The crude product was purified by silica gel column chromatography (dichlorobenzene:methanol = 20:1).Obtained a light yellow oil,Intermediate 8b,Yield: 73percent.

Reference： [1]Patent: CN108752322,2018,A .Location in patent: Paragraph 0117; 0120

82
[ 7583-53-1 ]
C₂₃H₁₆FN₅O [ No CAS ]
C₃₀H₃₀N₆O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%		Sodium hydride (60percent, 1.5 mmol) was added in portions at 0 °C.1-methylpiperidin-3-methanol (1.2 mmol)In a solution of N,N-dimethylformamide,Stir for 15 minutes,Then, the intermediate 4b was slowly added to the reaction solution at 0 ° C.Slowly warm to room temperature and stir for 1 hour.Add water to quench the reaction,Extracted with ethyl acetate,Drying the combined organic layers,concentrate,The crude product was purified by silica gel column chromatography (dichlorobenzene:methanol = 20:1).Obtained a light yellow oil,That is, the target 5b,Yield: 69percent.

Reference： [1]Patent: CN108752322,2018,A .Location in patent: Paragraph 0104; 0110

83
[ 7583-53-1 ]
C₂₀H₂₁Cl₃N₄O [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 7210 - 7232

84
[ 7583-53-1 ]
methyl 1-((1-methylpiperidin-3-yl)methyl)-1H-indole-6-carboxylate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 7210 - 7232

85
[ 7583-53-1 ]
3-(1-((1-methylpiperidin-3-yl)methyl)-1H-indol-6-yl)-3-oxopropanenitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 7210 - 7232

86
[ 7583-53-1 ]
3-amino-5-(1-((1-methylpiperidin-3-yl)methyl)-1H-indol-6-yl)-1H-pyrazole-4-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 7210 - 7232

87
[ 7583-53-1 ]
7-((2-methyl-[1,1’-biphenyl]-3-yl)methoxy)-5-((1-methylpiperidin-3-yl)methoxy)-2,3-dihydro-1H-indene-4-carbaldehyde [ No CAS ]

Reference： [1]Patent: WO2019/175897,2019,A1

88
[ 7583-53-1 ]
(2S)-1-((7-((2-methyl-[1,1‘-biphenyl]-3-yl)methoxy)-5-((1-methylpiperidin-3-yl)methoxy)-2,3-dihydro-1H-inden-4-yl)methyl)piperidine-2-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2019/175897,2019,A1

Same Skeleton Products

Related Products

Historical Records

Related Functional Groups of
[ 7583-53-1 ]

Alcohols

[ 37675-20-0 ]

(R)-(Piperidin-3-yl)methanol

Similarity: 0.92

[ 144539-77-5 ]

(S)-Piperidin-3-ylmethanol

Similarity: 0.92

[ 20691-89-8 ]

1-Methyl-4-piperidinemethanol

Similarity: 0.92

[ 90226-87-2 ]

(1-Ethylpiperidin-4-yl)methanol

Similarity: 0.92

[ 4606-65-9 ]

3-(Hydroxymethyl)piperidine

Similarity: 0.92

Related Parent Nucleus of
[ 7583-53-1 ]

Aliphatic Heterocycles

[ 37675-20-0 ]

(R)-(Piperidin-3-yl)methanol

Similarity: 0.92

[ 144539-77-5 ]

(S)-Piperidin-3-ylmethanol

Similarity: 0.92

[ 20691-89-8 ]

1-Methyl-4-piperidinemethanol

Similarity: 0.92

[ 90226-87-2 ]

(1-Ethylpiperidin-4-yl)methanol

Similarity: 0.92

[ 1210934-04-5 ]

(S)-(1-Methylpyrrolidin-3-yl)methanol

Similarity: 0.89

Piperidines

[ 37675-20-0 ]

(R)-(Piperidin-3-yl)methanol

Similarity: 0.92

[ 144539-77-5 ]

(S)-Piperidin-3-ylmethanol

Similarity: 0.92

[ 20691-89-8 ]

1-Methyl-4-piperidinemethanol

Similarity: 0.92

[ 90226-87-2 ]

(1-Ethylpiperidin-4-yl)methanol

Similarity: 0.92

[ 4606-65-9 ]

3-(Hydroxymethyl)piperidine

Similarity: 0.92

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 7583-53-1 ] {[proInfo.proName]}

Quality Control of [ 7583-53-1 ]

Related Doc. of [ 7583-53-1 ]

Product Details of [ 7583-53-1 ]

Calculated chemistry of [ 7583-53-1 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 7583-53-1 ]

Application In Synthesis of [ 7583-53-1 ]

[ 7583-53-1 ] Synthesis Path-Upstream 1~4

[ 7583-53-1 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 7583-53-1 ]

Alcohols

Related Parent Nucleus of [ 7583-53-1 ]

Aliphatic Heterocycles

Piperidines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 7583-53-1 ]

Related Parent Nucleus of
[ 7583-53-1 ]