[ CAS No. 7037-30-1 ] {[proInfo.proName]}

Name: 7037-30-1|3-(1-Methylpiperidin-4-yl)propan-1-ol|97%
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Quality Control of [ 7037-30-1 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 7037-30-1 ]

CAS No. :	7037-30-1	MDL No. :	MFCD06637513
Formula :	C₉H₁₉NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QYRYQOHCDCTGHJ-UHFFFAOYSA-N
M.W :	157.25	Pubchem ID :	15540677
Synonyms :

Safety of [ 7037-30-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 7037-30-1 ]

* 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 [ 7037-30-1 ]
Downstream synthetic route of [ 7037-30-1 ]

[ 7037-30-1 ] Synthesis Path-Upstream 1~5

1
[ 7037-49-2 ]
[ 50-00-0 ]
[ 7037-30-1 ]

Reference： [1] Journal of the American Chemical Society, 1947, vol. 69, p. 630,631
[2] Patent: US2008/306082, 2008, A1, . Location in patent: Page/Page column 6
[3] Patent: US2010/4450, 2010, A1, . Location in patent: Page/Page column 14

2
[ 154775-43-6 ]
[ 7037-30-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran for 3 h; Heating / reflux Stage #2: With water In tetrahydrofuran at 0 - 20℃; for 0.25 h; Stage #3: With sodium hydroxide; water In tetrahydrofuran at 0 - 20℃; for 18.25 h;	A. 3-(1-Methyl-piperidin-4-yl)-propan-1-ol. To a refluxing solution of 1 N lithium aluminum hydride in THF (40 mmol) was added dropwise a solution of N-BOC-4-piperidinepropionic acid (3.0 g, 11.6 mmol) in THF (30 mL). The reaction mixture was heated for 3 h and then cooled to rt. Upon further cooling to 0° C., water (1.5 mL) was added slowly, and the reaction mixture was allowed to warm to rt over 15 min. The mixture was again cooled to 0° C., and 10percent NaOH (1.5 mL) was added slowly. Upon warming up to rt over 15 min, the mixture was again cooled to 0° C. and more water (4.5 mL) was added. The resultant mixture was allowed to warm to rt over 18 h, and was then filtered through a diatomaceous earth pad. The filtrate was concentrated under reduced pressure, and the residue was purified by Method 2 to afford 1.9 g (100percent) of 3-(1-methyl-piperidin-4-yl)-propan-1-ol as a yellow oil. MS (electrospray): mass calculated for C₉H₁₉NO, 157.15; m/z found, 158.1 [M+H]⁺. ¹H NMR (400 MHz, CD₃OD): 3.45-3.41 (m, 2H), 2.77-2.74 (m, 2H), 1.89-1.85 (m, 2H), 1.64-1.61 (m, 2H), 1.47-1.43 (m, 2H), 1.21-1.12 (m, 5H).
100%	Stage #1: With lithium aluminium tetrahydride; water In tetrahydrofuran at 0 - 20℃; for 3 h; Heating / reflux Stage #2: With sodium hydroxide; water In tetrahydrofuran at 0 - 20℃; for 0.5 h;	To a refluxing solution of 1 M LiAlH₄ (40 mmol) in THF (30 mL) was added dropwise a solution of N-BOC-4-piperidinepropionic acid (3.0 g, 11.6 mmol). The reaction mixture was heated for 3 h then cooled to rt. Upon further cooling to 0° C., water (1.5 mL) was added slowly, and the reaction mixture was allowed to warm to rt over 15 min. The mixture was again cooled to 0° C., and 10percent aq. NaOH (1.5 mL) was added slowly. Upon warming to rt over 15 min, the mixture was cooled to 0° C. and more water (4.5 mL) was added. The resultant mixture was allowed to warm to rt over 18 h, and was then filtered through a pad of diatomaceous earth. The filtrate was concentrated, and the residue was purified by Method 1 to afford 1.9 g (100percent) of 3-(1-methyl-piperidin-4-yl)-propan-1-ol as a yellow oil. MS (ESI): mass calcd for C₉H₁₉NO, 157.15; m/z found 158.1 [M+H]⁺. ¹H NMR (400 MHz, CD₃OD): 3.45-3.41 (m, 2H), 2.77-2.74 (m, 2H), 1.89-1.85 (m, 2H), 1.64-1.61 (m, 2H), 1.47-1.43 (m, 2H), 1.21-1.12 (m, 5H).

Reference： [1] Patent: US2005/70550, 2005, A1, . Location in patent: Page/Page column 16-17
[2] Patent: US2005/261309, 2005, A1, . Location in patent: Page/Page column 17

3
[ 2629-72-3 ]
[ 50-00-0 ]
[ 7037-30-1 ]

Reference： [1] Patent: US2010/4450, 2010, A1, . Location in patent: Page/Page column 14

4
[ 108153-26-0 ]
[ 7037-30-1 ]

Reference： [1] Journal of the American Chemical Society, 1956, vol. 78, p. 4077,4080

5
[ 2629-72-3 ]
[ 7037-30-1 ]

Reference： [1] Journal of the American Chemical Society, 1956, vol. 78, p. 4077,4080
[2] Journal of the American Chemical Society, 1947, vol. 69, p. 630,631

[ 7037-30-1 ] Synthesis Path-Downstream 1~30

1
[ 7037-49-2 ]
[ 50-00-0 ]
[ 7037-30-1 ]

Yield	Reaction Conditions	Operation in experiment
		Preparation 153-(1-Methylpiperidin-4-yl)-propylamine(A). Preparation of 3-(1-methylpiperidin-4-yl)-propan-1-ol; Formalin (6.33 g, 211 mmol) is added to a stirred solution of 3-(piperidin-4-yl)-propan-1-ol (3.02 g, 21.1 mmol) in acetonitrile (30 mL) at ambient temperature. The solution is allowed to stir for 20 minutes. Sodium cyanoborohydride (3.31 g, 52.7 mmol) and acetic acid (3 mL) are sequentially added to the reaction mixture and the resultant mixture is stirred for another 2 hours. After concentration, the crude product is dissolved in dichloromethane (150 mL), washed with saturated aqueous NaHCO3 (60 mL.x.2), dried and concentrated. The crude product is subjected to chromatography on silica gel and eluted with 2 M NH3/CH3OH in dichloromethane 0-15percent to give the title compound as an oil (2.70 g).
	With hydrogen;5% rhodium-on-charcoal; In water; at 20 - 50℃; under 15514.9 Torr;	Example 3 1-Methyl-4-Piperidinepropanol An Argonaut reaction vessel was charged with 4-pyridinepropanol (500.0 mg, 3.49 mmol) and 5percent Rh/C (62percent wet, 300.0 mg) in water (4.00 g). The resultant slurry was stirred at 500 RPM and the unit was pressurized with 300 psi of hydrogen. The resultant mixture was heated at 50° C. for about 4-4.5 h, during which time the hydrogen uptake ceased. The resultant mixture was then cooled to room temperature and a 37percent formaldehyde solution (340.0 mg, 4.19 mmol) was added in a single portion. The Argonaut vessel was sealed and the resultant slurry was stirred at 500 RPM, the unit was repressurized with 300 psi of hydrogen, and heated to 50° C. Hydrogen uptake ceased in about 1.2-1.5 h to yield the title compound, which was used in the next step without further purification or isolation. HPLC-MS analysis of an aliquot showed only C9H19NO MS: (Cl): m/z 158 (M++1)

Reference： [1]Journal of the American Chemical Society,1947,vol. 69,p. 630,631
[2]Patent: US2008/306082,2008,A1 .Location in patent: Page/Page column 6
[3]Patent: US2010/4450,2010,A1 .Location in patent: Page/Page column 14

2
[ 7037-30-1 ]
[ 1871-76-7 ]
diphenyl-acetic acid-[3-(1-methyl-[4]piperidyl)-propyl ester] [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1947,vol. 69,p. 630,631

3
[ 7037-30-1 ]
[ 24168-51-2 ]
fluorene-9-carboxylic acid-[3-(1-methyl-[4]piperidyl)-propyl ester] [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1947,vol. 69,p. 630,631

4
[ 7037-30-1 ]
[ 26934-39-4 ]

Reference： [1]Journal of the American Chemical Society,1952,vol. 74,p. 1919

5
[ 108153-26-0 ]
[ 7037-30-1 ]

Reference： [1]Journal of the American Chemical Society,1956,vol. 78,p. 4077,4080

7
[ 7037-30-1 ]
[ 263149-10-6 ]
4-chloro-6-methoxy-7-[3-(1-methyl-piperidin-4-yl)-propoxy]-quinoline-3-carbonitrile [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 3797 - 3800

8
[ 7037-30-1 ]
[ 622369-46-4 ]
4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[3-(1-methylpiperidin-4-yl)propoxy]quinoline-3-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 1599 - 1601

9
[ 7037-30-1 ]
4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[3-(1-methylpiperidin-4-yl)propoxy]quinoline-3-carbonitrile [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 3797 - 3800

10
[ 2629-72-3 ]
[ 7037-30-1 ]

Reference： [1]Journal of the American Chemical Society,1956,vol. 78,p. 4077,4080
[2]Journal of the American Chemical Society,1947,vol. 69,p. 630,631

11
[ 7037-30-1 ]
4-(4,4-diphenyl-butyl)-1-methyl-piperidine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1952,vol. 74,p. 1919

12
[ 7037-30-1 ]
[ 857377-15-2 ]

Reference： [1]Journal of the American Chemical Society,1952,vol. 74,p. 1919

13
[ 7037-30-1 ]
2-isobutyl-5-(1-methyl-[4]piperidyl)-2-phenyl-valeronitrile [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1952,vol. 74,p. 1919

14
[ 7037-30-1 ]
[ 857385-32-1 ]

Reference： [1]Journal of the American Chemical Society,1952,vol. 74,p. 1919

15
[ 7037-30-1 ]
4-(4,4-diphenyl-butyl)-1,1-dimethyl-piperidinium; iodide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1952,vol. 74,p. 1919

16
[ 7037-30-1 ]
4-(4-cyclohexyl-4-phenyl-butyl)-1,1-dimethyl-piperidinium; iodide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1952,vol. 74,p. 1919

17
[ 154775-43-6 ]
[ 7037-30-1 ]

Yield	Reaction Conditions	Operation in experiment
100%		A. 3-(1-Methyl-piperidin-4-yl)-propan-1-ol. To a refluxing solution of 1 N lithium aluminum hydride in THF (40 mmol) was added dropwise a solution of N-BOC-4-piperidinepropionic acid (3.0 g, 11.6 mmol) in THF (30 mL). The reaction mixture was heated for 3 h and then cooled to rt. Upon further cooling to 0 C., water (1.5 mL) was added slowly, and the reaction mixture was allowed to warm to rt over 15 min. The mixture was again cooled to 0 C., and 10% NaOH (1.5 mL) was added slowly. Upon warming up to rt over 15 min, the mixture was again cooled to 0 C. and more water (4.5 mL) was added. The resultant mixture was allowed to warm to rt over 18 h, and was then filtered through a diatomaceous earth pad. The filtrate was concentrated under reduced pressure, and the residue was purified by Method 2 to afford 1.9 g (100%) of 3-(1-methyl-piperidin-4-yl)-propan-1-ol as a yellow oil. MS (electrospray): mass calculated for C9H19NO, 157.15; m/z found, 158.1 [M+H]+. 1H NMR (400 MHz, CD3OD): 3.45-3.41 (m, 2H), 2.77-2.74 (m, 2H), 1.89-1.85 (m, 2H), 1.64-1.61 (m, 2H), 1.47-1.43 (m, 2H), 1.21-1.12 (m, 5H).
100%		To a refluxing solution of 1 M LiAlH4 (40 mmol) in THF (30 mL) was added dropwise a solution of N-BOC-4-piperidinepropionic acid (3.0 g, 11.6 mmol). The reaction mixture was heated for 3 h then cooled to rt. Upon further cooling to 0 C., water (1.5 mL) was added slowly, and the reaction mixture was allowed to warm to rt over 15 min. The mixture was again cooled to 0 C., and 10% aq. NaOH (1.5 mL) was added slowly. Upon warming to rt over 15 min, the mixture was cooled to 0 C. and more water (4.5 mL) was added. The resultant mixture was allowed to warm to rt over 18 h, and was then filtered through a pad of diatomaceous earth. The filtrate was concentrated, and the residue was purified by Method 1 to afford 1.9 g (100%) of 3-(1-methyl-piperidin-4-yl)-propan-1-ol as a yellow oil. MS (ESI): mass calcd for C9H19NO, 157.15; m/z found 158.1 [M+H]+. 1H NMR (400 MHz, CD3OD): 3.45-3.41 (m, 2H), 2.77-2.74 (m, 2H), 1.89-1.85 (m, 2H), 1.64-1.61 (m, 2H), 1.47-1.43 (m, 2H), 1.21-1.12 (m, 5H).

Reference： [1]Patent: US2005/70550,2005,A1 .Location in patent: Page/Page column 16-17
[2]Patent: US2005/261309,2005,A1 .Location in patent: Page/Page column 17

18
[ 7037-30-1 ]
[ 124-63-0 ]
C₁₀H₂₁NO₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A. 4-[3-(4-Bromo-3-[1,3]dioxan-2-yl-phenoxy)-Propyl]-1-methyl-piperidine. To a solution of <strong>[7037-30-1]3-(1-methyl-piperidin-4-yl)-propan-1-ol</strong> (7.07 g, 45 mmol, 1.0 equiv) and methanesulfonyl chloride (4.18 mL, 54 mmol, 1.2 equiv) in dichloromethane (100 mL) at 0 C. was added triethylamine (9.41 mL, 68 mmol, 1.5 equiv). The reaction mixture, which was allowed to warm to rt, was stirred for 30 min and then poured into satd. aq. NaHCO3. The aqueous mixture was extracted with chloroform and then ethyl acetate. The combined extracts were dried (Na2SO4), filtered, and concentrated. The residue was dissolved in acetonitrile (100 mL) and 4-bromo-3-[1,3]dioxan-2-yl-phenol (11.7 g, 45 mmol, 1.0 equiv) and cesium carbonate (29.2 mg, 90 mmol, 2.0 equiv) were added. The mixture was stirred at rt for 12 h, then warmed to 50 C. for 1.0 h. The mixture was poured into satd. aq. NaHCO3 and extracted with ethyl acetate (2*) and chloroform. The combined extracts were dried (Na2SO4), filtered, and concentrated. Purification by Method 2 afforded 4.82 g (27%) of the title compound. 1H NMR (400 MHz, CD3OD): 7.43 (d, J=8.8 Hz, 1H), 7.19 (d, J=3.1 Hz, 1H), 6.83 (dd, J=8.8, 3.1 Hz, 1H), 5.72 (s, 1H), 4.27-4.19 (m, 2H), 4.10-4.00 (m, 2H), 3.97 (t, J=6.4 Hz, 2H), 2.93-2.85 (m, 2H), 2.28 (s, 3H), 2.25-2.11 (m, 1H), 2.07-1.97 (m, 2H), 1.85-1.72 (m, 4H), 1.52-1.21 (m, 6H).

Reference： [1]Patent: US2005/70550,2005,A1 .Location in patent: Page/Page column 59

19
[ 7037-30-1 ]
[ 56962-11-9 ]
[ 848847-25-6 ]

Yield	Reaction Conditions	Operation in experiment
80%	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 20℃; for 16h;	B. 2-Chloro-4-[3-(1-methyl-piperidin-4-yl)-propoxy]-benzaldehyde. To an ice-cooled solution of 2-chloro-4-hydroxybenzaldehyde (507 mg, 3.2 mmol, 1.0 equiv), triphenylphosphine (1.02 g, 3.9 mmol, 1.2 equiv), and <strong>[7037-30-1]3-(1-methyl-piperidin-4-yl)-propan-1-ol</strong> (508 mg, 3.9 mmol, 1.2 equiv) in THF (15 mL) was added diethyl azodicarboxylate (DEAD; 0.6 mL, 3.2 mmol, 1.0 equiv). The reaction mixture was allowed to warm to rt and was stirred for 16 h. The mixture was diluted with water and extracted three times with ethyl acetate. The combined extracts were dried (Na2SO4) and concentrated. Purification by Method 2 afforded 768 mg (80%) of the desired aldehyde. MS (electrospray): mass calculated for C16H23NO2, 261.17; m/z found, 262.2 [M+H]+. 1H NMR (400 MHz, CDCl3): 9.85 (s, 1H), 7.80 (d, J=8.6 Hz, 2H), 6.97 (d, J=8.6 Hz, 2H), 4.01 (t, J=6.4 Hz, 2H), 2.84-2.82 (m, 2H), 2.25 (s, 3H), 1.92-1.78 (m, 4H), 1.71-1.69 (m, 2H), 1.41-1.37 (m, 2H), 1.29-1.26 (m, 3H).

Reference： [1]Patent: US2005/70550,2005,A1 .Location in patent: Page/Page column 17

20
[ 7037-30-1 ]
[ 622369-82-8 ]
[ 753005-93-5 ]

Yield	Reaction Conditions	Operation in experiment
		A mixture of 4-[(2, 4-dichloro-5-methoxyphenyl) amino]-6-ethoxy-7-fluoro-3- quinolinecarbonitrile (200 mg, 0.49 mmol) and 3- (1-methyl-4-piperidinyl) propanol (154 mg, 0.98 mmol)) in 5 mL of N, N-dimethylformamide was heated at 125C for 5 min. Sodium hydride (60%) (98 mg, 2.45 mmol) was added and the mixture was heated at 125C for 1 hour. Additional sodium hydride (98 mg, 2.45 mmol) was added and the mixture was heated at 125C for 2 hours. The reaction mixture was cooled to room temperature and poured into saturated sodium bicarbonate and stirred for 1 hour. The precipitate was collected, washed with water and dried in vacuo. The residue was purified by preparative thin layer chromatography, developing with 15% methanol in dichloromethane. Trituation with diethyl ether provided 146 mg of 4- [ (2, 4-dichloro-5-methoxyphenyl) amino]-6-ethoxy-7- [3- (1- methylpiperidin-4-yl) propoxy] quinoline-3-carbonitrile as an off-white solid, mp 148- 151C. MS 543.2 (M+H) + Analysis for C28H32CI2N403-1. 8 H20 Calcd : C, 58.39 ; H, 6.23 ; N, 9.73. Found: C, 58.40 ; H, 6.16 ; N, 9.64.

Reference： [1]Patent: WO2005/47259,2005,A1 .Location in patent: Page/Page column 31-32

21
[ 7037-30-1 ]
[ 41438-18-0 ]
4-[3-(1-methyl-piperidin-4-yl)-propoxy]-benzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With di-tert-butyl-diazodicarboxylate; In tetrahydrofuran; at 0 - 20℃; for 16h;	To an ice-cooled solution of <strong>[41438-18-0]2-methyl-4-hydroxybenzaldehyde</strong> (722 mg, 5.3 mmol), PPh3 polymer resin (3 mmol/g, 2.2 g, 6.4 mmol), and 3-(1-methyl-piperidin-4-yl)-propan-1-ol (833 mg, 5.3 mmol, 1.0 equiv) in THF (25 mL) was added di-tert-butyl-azodicarboxylate (1.47 g, 6.4 mmol). The reaction mixture was allowed to warm to rt and was stirred for 16 h. The mixture was filtered through diatomaceous earth, diluted with water, and extracted three times with EtOAc. The combined extracts were dried (Na2SO4) and concentrated. Purification by Method 1 afforded 578 mg (40%) of the desired aldehyde. MS (ESI): mass calcd for C16H23NO2, 261.17; m/z found, 262.2 [M+H]+. 1H NMR (400 MHz, CDCl3): 9.85 (s,1H), 7.80 (d, J=8.6, 2H), 6.97 (d, J=8.6, 2H), 4.01 (t, J=6.4, 2H), 2.84-2.82 (m, 2H), 2.25 (s, 3H), 1.92-1.78 (m, 4H), 1.71-1.69 (m, 2H), 1.41-1.37 (m, 2H), 1.29-1.26 (m, 3H).

Reference： [1]Patent: US2005/261309,2005,A1 .Location in patent: Page/Page column 17

22
[ 7037-30-1 ]
[ 174709-17-2 ]
4-[(3-bromophenyl)amino]-7-[3-(1-methylpiperidin-4-yl)propyloxy]-6-nitroquinazoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; (2S)-N-methyl-1-phenylpropan-2-amine hydrate;	EXAMPLE II 4-[(3-Bromophenyl)amino]-7-[3-(1-methylpiperidin-4-yl)propyloxy]-6-nitroquinazoline To a solution of 1.45 g of <strong>[7037-30-1]3-(1-methylpiperidin-4-yl)propan-l-ol</strong> in 40 ml of tetrahydrofuran are added 360 mg of sodium hydride. The white suspension formed is stirred for 15 minutes at 65 C., cooled and mixed with 1.45 g of 4-[(3-bromophenyl)amino]-7-fluoro-6-nitroquinazoline, whereupon the mixture suddenly turns dark red. The reaction mixture is stirred first for 10 minutes at ambient temperature, then for 45 minutes at 65 C. As the reaction is not yet complete, a further 150 mg of sodium hydride are added and the mixture is stirred for a further 45 minutes at 65 C. The solvent is distilled off using a rotary evaporator and the brown residue is stirred with 50 ml of ice water. The aqueous phase is extracted with methylene chloride. The combined extracts are washed with water, dried over sodium sulfate and concentrated by evaporation. The crude product is purified by chromatography over a silica gel column with methylene chloride/methanol/concentrated ammonia solution (90:10:0.05). Yield: 1.30 g of (65% of theory); Rf value: 0.28 (silica gel, methylene chloride/methanol/concentrated aqueous ammonia solution=90:10:0.1); mass spectrum (ESI+): m/z=500, 502 [M+H]+.

Reference： [1]Patent: US2002/169180,2002,A1

23
[ 7037-30-1 ]
[ 33252-28-7 ]
[ 848848-60-2 ]

Yield	Reaction Conditions	Operation in experiment
76%		To a stirred solution of <strong>[7037-30-1]3-(1-methyl-piperidin-4-yl)-propan-1-ol</strong> (5.0 g, 31.7 mmol) in DMF (200 mL), was added NaH (60%; 1.73 g, 43.3 mmol) portion wise. Once the initial effervescence had subsided, the mixture was heated at 60 C. for 1 h, and then was cooled to rt. A solution of 6-chloronicotinonitrile (4.0 g, 28.9 mmol) in DMF (20 mL) was then added and the mixture was stirred for 16 h before quenching with saturated (satd.) aq. NaHCO3 (50 mL) and brine (50 mL). A precipitate was formed and was collected by vacuum filtration to afford 3.67 g of the product. The filtrate was concentrated to half the volume and a second crop of precipitate was recovered. The precipitates were combined to give 5.64 g (76%) of an orange solid, which was used without further purification. MS (ESI): mass calcd for C15H21N3O, 259.17; m/z found, 260.4 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.46 (dd, J=2.3, 0.8, 1H), 7.77 (dd, J=8.6, 2.3, 1H), 6.80 (dd, J=8.6, 0.8, 1H), 4.34 (t, J=6.6, 2H), 2.96-2.82 (m, 2H), 2.25 (s, 3H), 1.92-1.68 (m, 7H), 1.37-1.34 (m, 2H), 0.89-0.81 (m, 2H).

Reference： [1]Patent: US2005/261309,2005,A1 .Location in patent: Page/Page column 20

24
[ 7037-30-1 ]
[ 322474-21-5 ]
[ 1202680-07-6 ]

Yield	Reaction Conditions	Operation in experiment
	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 2 - 20℃;	Example 29 N-[3-(1-methylpiperidin-4-yl)-propyl]-N,N'-di-Boc-methylisothiourea To a 25 mL round bottom flask were added <strong>[7037-30-1]3-(1-methyl-piperidin-4-yl)-propan-1-ol</strong> (0.23 g, 0.0014 mol), 1,3-di-Boc-2-methylisothiourea (0.42 g, 0.0014 mol), PPh3 (0.42 g, 0.0016 mol) and THF (anhydrous, 8.0 mL). The resultant, stirred stirring solution was cooled to 2.0 C. To the resultant solution was then added DEAD (0.27 mL, 0.0016 mol) drop wise. The reaction was aged cold for 30 min, warmed to room temperature and aged for 14 h. The THF was removed via rotovap and the residue taken up in MTBE (10 mL). The resultant solution was extracted with saturated aqueous NaHCO3 (2*10 mL) and diluted with hexanes (20 mL). After 10 min, the resultant slurry was filtered and the filtrate concentrated via rotovap. The residue was taken up in hexanes (25 mL) and filtered after 10 min. The filtrate was concentrated to yield N-[3-(1-methylpiperidin-4-yl)-propyl]-N,N'-di-Boc-methylisothiourea. 1H-NMR: (400 MHz, CDCl3) delta, 3.50-3.43 (m, 2H), 2.87-2.79 (m, 2H), 2.40 (s, 3H), 2.24 (s, 3H), 1.86 (t, J=10.9 Hz, 2H), 1.72-1.60 (m, 4H), 1.53-1.45 (m, 18H), 1.28-1.20 (m, 5H). MS (electrospray): exact mass calculated for C21H39N3O4S, 429.27; m/z found, 430.2 [M+H]+

Reference： [1]Patent: US2010/4450,2010,A1 .Location in patent: Page/Page column 23

25
[ 7037-30-1 ]
[ 216584-22-4 ]
[ 1202680-06-5 ]

Yield	Reaction Conditions	Operation in experiment
	With diethylazodicarboxylate; In tetrahydrofuran; at 2 - 20℃; for 4.16667h;	Example 27 N-[3-(1-methylpiperidin-4-yl)-propyl]-N,N',N"-tri-Boc-guanidine To a 100 mL, 3-neck, round bottom flask were added <strong>[7037-30-1]3-(1-methyl-piperidin-4-yl)-propan-1-ol</strong> (1.91 g, 0.012 mol), Polymer Labs (Varian) PL-TPP resin (9.83 g, 0.014 mol), N,N',N"-tri-Boc-guanidine (4.36 g, 0.012 mol) and THF (anhydrous, 100 mL). The resultant mixture was stirred and cooled to 2 C., at which time DEAD (2.53 g, 0.014 mol) was added drop wise over 10 min. Upon completion of addition, the flask was warmed to room tempertaure, aged for 4 h and filtered to remove the resin bound oxide. The resultant cake was rinsed with THF (25 mL) and heptane (225 mL). The filtrates were combined, extracted with saturated aqueous NaHCO3 (225 mL), dried over anhydrous MgSO4, filtered and concentrated. The resultant residue was triturated in hot ethanol (25 mL), cooled to room temperature and filtered. The filtrate was concentrated to yield N-[3-(1-methylpiperidin-4-yl)-propyl]-N,N',N"-tri-Boc-guanidine. 1H-NMR: (400 MHz, CDCl3) delta, 10.64 (brs,1H), 3.75 (t, J=7.1 Hz, 2H), 2.83-2.80 (m, 2H), 2.24 (s, 3H), 1.87 (t, J=10.1 Hz, 2H), 1.72-1.63 (m, 4H), 1.54-1.46 (m, 27H), 1.30-1.18 (m, 5H). MS (electrospray): exact mass calculated for C25H46N4O6, 498.34; m/z found, 499.4 [M+H]+

Reference： [1]Patent: US2010/4450,2010,A1 .Location in patent: Page/Page column 22

26
[ 2629-72-3 ]
[ 50-00-0 ]
[ 7037-30-1 ]

Yield	Reaction Conditions	Operation in experiment
		Example 4 ; 1-Methyl-4-Piperidinepropanol An Argonaut reaction vessel was charged with 4-pyridinepropanol (500.0 mg, 3.49 mmol), methanol (6 mL), acetic acid (2 mL), and 10% P/C (dry, 77 mg). The resultant slurry was stirred at 500 RPM and the unit was pressurized with 300 psi of hydrogen at 35 C. The resultant mixture was then stirred for 8 hours (until the hydrogen uptake was observed to cease).The resultant mixture was then cooled to room temperature and a 37% formaldehyde solution (340.0 mg, 4.19 mmol) was added in a single portion. The Argonaut vessel was sealed and the resultant slurry was stirred at 500 RPM, the unit was re-pressurized with 300 psi of hydrogen, and heated to 35 C. Hydrogen uptake was observed to cease after about 20 min. The resultant mixture was filtered through a Celiteo pad to remove the catalyst. The resultant solution was cooled to 0 C., and 50% NaOH solution was added to adjust the pH>12. The resultant mixture was then concentrated in vacuo, and the residue extracted with 2-Me-THF (3×10 mL). The combined organic phases was washed with brine (5 mL), dried (MgSO4), and concentrated in vacuo to yield the title compound.MS: (Cl): m/z 158 (M++1)

Reference： [1]Patent: US2010/4450,2010,A1 .Location in patent: Page/Page column 14

27
[ 7037-30-1 ]
[ 1202679-99-9 ]
[ 1202680-00-9 ]

Yield	Reaction Conditions	Operation in experiment
	With di-isopropyl azodicarboxylate; triphenylphosphine; In 2-methyltetrahydrofuran; at 0 - 20℃;	STEP A: (5-Cyano-4-methyl-pyrimidin-2-yl)-[3-(1-methyl-piperidin-4-yl)-propyl]-carbamic acid ethyl ester A 50 ml Erlenmeyer flask was charged with <strong>[7037-30-1]3-(1-methyl-piperidin-4-yl)-propan-1-ol</strong> (1.5 g, 9.42 mmol) followed by addition of 2-methyltetrahydrofuran (1.72 g). Anhydrous magnesium sulfate (0.7 g) was then added and the resultant suspension was stirred for 5 minutes. The solid was filtered off and washed with 2-methyltetrahydrofuran (2.0 g). The water content of the filtrate was determined to be KF=0.66%. The filtrate was transferred to a 100 ml 3-neck flask equipped with a stirrer, a thermocouple and an addition funnel followed by addition of triphenylphosphine (3.2 g, 12.1 mmol) and (5-cyano-4-methyl-pyrimidin-2-yl)-carbamic acid ethyl ester (2.0 g, 9.65 mmol). The resultant suspension was cooled to about 0-5 C. Diisopropyl azodicarboxylate (2.55 g, 11.98 mmol) was added via the addition funnel to the stirred suspension over about 1 h, while maintaining the temperature at about 0-5 C. After the addition, the resultant mixture was stirred at ambient temperature overnight. The reaction was monitored by HPLC. The reaction mixture was quenched at about 20-30 C. with an HCl solution [prepared from 37% HCl (3.48 g, 34.8 mmol) and water (14.0 g, 777.8 mmol)]. The resultant biphasic mixture was cooled to ambient temperature and allowed to settle. The top organic layer was split off and the bottom aqueous layer was extracted with toluene (8.71 g). The aqueous layer was basified at ambient temperature by addition of a sodium hydroxide solution [prepared from NaOH (0.8 g, 20.0 mmol) and water (5.0 g)]. The desired product-(5-cyano-4-methyl-pyrimidin-2-yl)-[3-(1-methyl-piperidin-4-yl)-propyl]-carbamic acid ethyl ester-was extracted with 2-methyltetrahydrofuran (17.2 g,). The organic layer was dried over anhydrous magnesium sulfate (4.0 g) and the solvent was removed by rotary evaporation to yield (5-cyano-4-methyl-pyrimidin-2-yl)-[3-(1-methyl-piperidin-4-yl)-propyl]-carbamic acid ethyl ester. MS: (Cl): m/z 346 (M++1).

Reference： [1]Patent: US2010/4450,2010,A1 .Location in patent: Page/Page column 15

28
[ 7037-30-1 ]
[ 1202680-01-0 ]
[ 1202680-02-1 ]

Yield	Reaction Conditions	Operation in experiment
	With di-isopropyl azodicarboxylate; triphenylphosphine; In 2-methyltetrahydrofuran; at 0 - 20℃;	STEP A: (5-Cyano-4-methyl-pyrimidin-2-yl)-[3-(1-methyl-piperidin-4-yl)-provyl]-carbamic acid tert-butyl esterA 200 ml Erlenmeyer flask was charged with <strong>[7037-30-1]3-(1-methyl-piperidin-4-yl)-propan-1-ol</strong> (12.75 g, 80.11 mmol) followed by 2-methyltetrahydrofuran (146.0 g). Magnesium sulfate was added and the resultant suspension was stirred for 5 minutes. The solid was filtered off and washed with 2-methyltetrahydrofuran (14.6 g). The water content of the filtrate was determined to be KF=0.66%.The filtrate was transferred to a 500 ml 3-neck flask equipped with an overhead stirrer, a thermocouple, and an addition funnel. Triphenylphosphine (30.2 g, 113.99 mmol) was added followed by addition of (5-cyano-4-methyl-pyrimidin-2-yl)-carbamic acid tert-butyl ester (17.0 g, 71.48 mmol). The resultant mixture was stirred until the solids were observed to dissolve. The resultant solution was cooled to about 0-5 C. and diisopropyl azodicarboxylate (DIAD) (23.91 g, 112.33 mmol) was added via the addition funnel to the stirred solution over 50 minutes, while maintaining the temperature at about 0-5 C. After the addition, the resultant mixture was warmed to ambient temperature and stirred overnight. The reaction was monitored by HPLC. (5-Cyano-4-methyl-pyrimidin-2-yl)-[3-(1-methyl-piperidin-4-yl)-propyl]-carbamic acid tert-butyl ester, in the resultant solution was used in the next step without further isolation and/or purification.

Reference： [1]Patent: US2010/4450,2010,A1 .Location in patent: Page/Page column 17

29
[ 7037-30-1 ]
[ 1202680-03-2 ]
[ 1202680-09-8 ]

Yield	Reaction Conditions	Operation in experiment
	With di-isopropyl azodicarboxylate; triphenylphosphine; In ethyl acetate; at 0 - 25℃;	Example 12 4-Methyl-2-[3-(1-methyl-piperidin-4-yl)-propylamino]-pyrimidine-5-carbonitrile A 100ml 3-neck flask equipped with a magnetic stir-bar, a thermocouple and an addition funnel was charged with N-(5-cyano-4-methyl-pyrimidin-2-yl)-acetamide (1.00 g, 5.39 mmol) followed by EtOAc (9.02 g). The resultant mixture was stirred to yield a solution and then <strong>[7037-30-1]3-(1-methyl-piperidin-4-yl)-propan-1-ol</strong> (1.70 g, 10.81 mmol) was added, followed by addition of Ph3P (2.85 g, 10.76 mmol). The resultant solution was cooled to 0-5 C. and diisopropyl azodicarboxylate (DIAD) (2.30 g, 10.81 mmol) was added using the addition funnel, while maintaining the reaction temperature below 10 C. After the addition was complete, the resultant mixture was warmed to ambient temperature and stirred at 20-25 C. overnight. The resultant mixture was treated at 20-25 C. with a dilute HCl solution (37% HCl (4.80 g) diluted with water (15.00 g)), followed by EtOAc (9.02 g) and water (10.00 g). The resultant mixture was settled and the top organic layer was removed. The acidic aqueous layer was stirred at room temperature for 1 h to yield a mixture (which contained the hydrolysis product, N-(5-cyano-4-methyl-pyrimidin-2-yl)-N-[3-(1-methyl-piperidin-4-yl)-propyl]-acetamide). The aqueous layer was extracted one time with EtOAc (9.02 g).

Reference： [1]Patent: US2010/4450,2010,A1 .Location in patent: Page/Page column 17-18

30
[ 7037-30-1 ]
[ 10065-79-9 ]
[ 1202680-04-3 ]

Yield	Reaction Conditions	Operation in experiment
	With di-isopropyl azodicarboxylate; triphenylphosphine; In 2-methyltetrahydrofuran; at -10 - 50℃;Inert atmosphere;Product distribution / selectivity;	Example 14 N-[3-(1-methylpiperidin-4-yl)-propyl]-N,N'-di-cbz-guanidine To a 20 L carboy was charged 2-methyl-THF (8.00 kg) and <strong>[7037-30-1]3-(1-methylpiperidin-4-yl)propan-1-ol</strong> (2.80 kg 17.62 mol). To the resultant solution were added molecular sieves (0.28 kg) and the resultant slurry was stirred until the water content was below 0.1% as tested by KF. The resultant solution was then filtered over Celite and then charged to a 100 L glass-lined reactor, with 2-methyl-THF (17.52 kg) added. Triphenylphosphine (5.38 kg, 20.29 kg), and N,N'-di-Cbz-guanidine (5.77 kg 17.62 mol) were charged under a nitrogen blanket to the stirring solution. The reactor walls were rinsed with 2-methyl-THF (2.00 kg). The resultant suspension was cooled to between about -10 and about 0 C. and a solution of diisopropyl azodicarboxylate (4.41 kg 20.26 mol) and 2-methyl-THF (8.00 kg) was added while keeping the reaction temperature below 50 C. The resultant solution was then slowly warmed to about 15-20 C. over a 30-minute period. After reaction completion a pre-made solution of 36.5% hydrochloric acid (2.61 kg 26.12 mol) and purified water (25.70 kg) was added at a temperature of about 15-20 C. Toluene (15.80 kg) was added, the resultant mixture was then stirred for 15 minutes and settled for 20 minutes. The water layer was retained and the 2-methyl-THF/toluene layer was discarded. The resultant mixture was extracted sequentially three times with toluene (35.0 kg), discarding the toluene layer after each extraction. To the extracted water/product layer in the 100 L reactor was added ethanol (200 proof, 4.42 kg) and purified water (48.00 kg). To the resultant, stirring solution was added 6N sodium hydroxide (5.54 kg 29.10 mol) slowly while keeping the temperature between about 15-20 C. The resultant suspension was stirred for 1 hour, filtered and washed with purified water (29.00 kg). The wet solids were dried in a vacuum oven at about 40-45 C. to yield the title compound.

Reference： [1]Patent: US2010/4450,2010,A1 .Location in patent: Page/Page column 18-19

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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
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H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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Health hazards
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H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
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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
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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
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H332	Harmful if inhaled
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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. 7037-30-1 ] {[proInfo.proName]}

Quality Control of [ 7037-30-1 ]

Related Doc. of [ 7037-30-1 ]

Product Details of [ 7037-30-1 ]

Safety of [ 7037-30-1 ]

Application In Synthesis of [ 7037-30-1 ]

[ 7037-30-1 ] Synthesis Path-Upstream 1~5

[ 7037-30-1 ] Synthesis Path-Downstream 1~30

Related Functional Groups of [ 7037-30-1 ]

Alcohols

Related Parent Nucleus of [ 7037-30-1 ]

Aliphatic Heterocycles

Piperidines

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[ 7037-30-1 ]

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[ 7037-30-1 ]