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Quality Control of [ 34375-89-8 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 34375-89-8 ]

CAS No. :	34375-89-8	MDL No. :	MFCD07383543
Formula :	C₅H₁₁N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	85.15	Pubchem ID :	-
Synonyms :

Safety of [ 34375-89-8 ]

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Hazard Statements:	H302+H332-H314-H226	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 34375-89-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 34375-89-8 ]

[ 34375-89-8 ] Synthesis Path-Downstream 1~11

1
[ 34375-89-8 ]
[ 13532-18-8 ]
3-Methyl-1-<3-(methylthio)propyl>pyrrolidin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With lithium aluminium tetrahydride In diethyl ether for 22h; Heating;

Reference： [1]Reder; Veith; Buschinger [Helvetica Chimica Acta, 1995, vol. 78, # 1, p. 73 - 79]

2
[ 2555-05-7 ]
[ 34375-89-8 ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4388 - 4397
[2]Helvetica Chimica Acta,1995,vol. 78,p. 73 - 79

3
[ 34375-89-8 ]
[ 85953-29-3 ]
[ 313674-10-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 9524 - 9535
[2]Journal of Medicinal Chemistry,2000,vol. 43,p. 4388 - 4397

4
[ 34375-89-8 ]
[ 29969-57-1 ]
2-(3-methyl-pyrrolidin-1-yl)-6-nitro-quinoline [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5270 - 5274

5
[ 34375-89-8 ]
[ 228251-24-9 ]
[ 742100-76-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In water; dimethyl sulfoxide; at 75℃; for 2h;	Reference Example 155 A suspension of <strong>[228251-24-9]5-bromo-2-chloronicotinaldehyde</strong> (1.2 g), 3-methylpyrrolidine (928 mg) and sodium carbonate (1.16 g) in DMSO (40 ml) and water (20 ml) was stirred for 2 hours at 75C under a nitrogen atmosphere. After returning to room temperature, water was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and then the resulting residue was separated and purified by silica gel column chromatography (hexane: ethyl acetate = 20: 1 ? hexane: ethyl acetate = 4: 1). The resulting solids were washed with hexane to give 5-bromo-2-(3-methylpyrrolidin-1-yl)nicotinaldehyde (761 mg) as yellow crystals. m.p. 72.0-73.0C. 1H-NMR (300 MHz, CDCl3) delta 1.13 (3H, d, J=6.6 Hz), 1.53-1.67 (1H, m), 2.07-2.16 (1H, m), 2.28-2.41 (1H, m), 3.17-3.24 (1H, m), 3.46-3.56 (2H, m), 3.61-3.70 (1H, m), 8.01 (1H, d, J=2.4 Hz), 8.31 (1H, d, J=2.4 Hz), 9.96 (1H, s). Elementary analysis C11H13N2OBr, Calcd. C, 49.09; H, 4.87; N, 10.41: Found C, 49.07; H, 4.88; N, 10.29.

Reference： [1]Patent: EP1593673,2005,A1 .Location in patent: Page/Page column 98

6
[ 34375-89-8 ]
[ 2555-05-7 ]
[ 459448-85-2 ]
[ 459448-88-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium iodide; potassium carbonate; In acetonitrile;	Example 4 2-Methyl-5-[2-(3-methyl-pyrrolidin-1-yl)-ethoxy]-1H-indole-3-carboxylic Acid Benzyl Ester To a mixture of 5-(2-chloro-ethoxy)-2-methyl-1H-indole-3-carboxylic acid benzyl ester (0.873 mmol, 0.300 g, Example 1, Step A) in 8.76 mL of acetonitrile was added potassium carbonate (0.873 mmol, 0.120 g), potassium iodide (0.0873 mmol, 0.015 g), and 3-methyl-pyrrolidine (11.74 mmol, 1.00 g, prepared from 3-methyl-pyrrolidin-2-one, Lancaster, according to Reder E.; et al. Helv. Chim. Acta 1995;78:73). The mixture was heated at reflux for 70 hours, cooled to room temperature, and concentrated. The residue was partitioned between ethyl acetate (30 mL) and water (30 mL), the layers were separated, and the aqueous phase was extracted with ethyl acetate (3*20 mL). These extracts were washed with saturated aqueous NaCl (20 mL), dried over MgSO4, and concentrated to a dark brown oil (0.558 g). The product was purified by silica gel flash column chromatography (0-5% Et3N/ethyl acetate) and triturated with ether to afford pure product as a cream colored solid (0.167 g, 49%): mp 121-122 C.; IR (KBr) 3305, 2954, 2923, 1663, 1485, 1453, 1179 cm-1; 1H-NMR (400 MHz, CDCl3) delta 1.03 (d, J=6.59 Hz, 3H, CHCH3), 1.34-1.43 (m, 1H, CHCH3), 2.01-2.12 (m, 1H, aliphatic CH), 2.15-2.23 (m, 1H, aliphatic CH), 2.25-2.39 (m, 1H, CHN), 2.61-2.70 (m, 1H, CHN), 2.69 (s, 3H, ArCH3), 2.83-3.00 (m, 3H, CH2N), 3.01-3.11 (m, 1H, CHN), 4.05-4.12 (m, 2H, CH2OAr), 5.36 (s, 2H, CO2CH2Ph), 6.75-6.77 (m, 1H, ArH), 7.12 (d,J=8.79 Hz, 1H, ArH), 7.31 (d,J=7.08 Hz, 1H, ArH), 7.34-7.38 (m, 2H, ArH), 7.47 (d, J=8.06 Hz, 2H, ArH), 7.54 (s, 1H, ArH), 8.47 (s, 1H, NH); MS(APCI+): m/z 393.1 (M+1). Anal. Calcd for C24H28N2O3: C, 73.44; H, 7.19; N, 7.14. Found: C, 73.08; H, 7.13; N, 7.05.

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

7
[ 34375-89-8 ]
[ 108-77-0 ]
[ 98-44-2 ]
[ 107-15-3 ]
[ 1059230-75-9 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1,3,5-trichloro-2,4,6-triazine; amino-benzene-1,4-disulfonic acid With sodium hydroxide In water at 0 - 25℃; for 4h; Stage #2: 3-methylpyrrolidin In water for 2h; Stage #3: ethylenediamine	19.1 To 150 parts of ice water, 18.4 parts of cyanuric chloride and 0.2 parts of LEOCOL TD-90 (which is the trade name of a surfactant manufactured by Lion Corporation) were added, and stirred at 10°C or below for 30 minutes. Next, 31.3 parts of 2,5-disulfoaniline (purity: 90.5%) was added thereto, and reacted at 0 to 25°C for 4 hours while adjusting the pH of the resulting liquid to 3.0 using a 10% aqueous sodium hydroxide solution. Next, 10.9 parts of 3-methylpyrrolidine was added dropwise to the reaction liquid, and after that, reaction was conducted for 2 hours. The liquid temperature was controlled at 50°C, 60.1 parts of ethylenediamine was added thereto and stirred overnight at room temperature, and then the liquid temperature was controlled at 50°C. The liquid volume at that time was 620 parts. To this reaction liquid, 124 parts of sodium chloride was added, and dissolved, and then the pH was adjusted to 1.0 with concentrated hydrochloric acid, followed by stirring for 30 minutes to precipitate crystals. The precipitated crystals were filtered to obtain 68.1 parts of a wet cake. The obtained wet cake was put into a beaker, 340 parts of water was further added, and the pH of the resulting suspension was adjusted to 9.0 using a 10% aqueous sodium hydroxide solution, to dissolve the wet cake. At this time, the liquid volume was 420 parts. To this solution, 84 parts of sodium chloride was added, and then the pH of the liquid was controlled at 1.0 using concentrated hydrochloric acid, followed by stirring for 30 minutes to precipitate crystals. The precipitated crystals were filtered to obtain 100 parts of a wet cake. The obtained wet cake was put into a beaker, 300 parts of methanol and 200 parts of water were further added and stirred at 50°C for 1 hour. The resulting suspension was filtered to obtain 37.1 parts of a wet cake. The obtained wet cake was dried to obtain 30.1 parts of a compound of the above formula (47) as white powder.

Reference： [1]Current Patent Assignee: NIPPON KAYAKU CO LTD - EP2128202, 2009, A1 Location in patent: Page/Page column 52

8
[ 34375-89-8 ]
[ 45470-22-2 ]
[ 44565-27-7 ]
[ 106-94-5 ]
[ 90076-65-6 ]
[ 1415219-11-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; formaldehyd; formic acid; magnesium sulfate; triphenylphosphine; In tetrachloromethane; dichloromethane; water, 1,3-dimethyl-1-propylpyrrolidinium bromide; water;	EXAMPLE 1 In this example, a method for producing 1,3-dimethyl-1-propylpyrrolidinium bis(trifluoromethanesulfonyl)amide (abbreviation: 3mP13-TFSA) represented by the structural formula (200) is described. First, <strong>[44565-27-7]4-amino-2-methyl-1-butanol</strong> (24.8 g, 240 mmol) and carbon tetrachloride (111 g, 720 mmol) were mixed under a nitrogen atmosphere at room temperature. Into this mixture, triphenylphosphine (69.2 g, 264 mmol) dissolved in dehydrated dichloromethane (150 ml) was added. Stirring was performed at 40 C. for 1 to 1.5 hours, and then pure water (50 ml) was added to the reacted solution and stirred well. Subsequently, an aqueous phase and a dichloromethane phase were separated. A yellow oily substance was extracted from the dichloromethane phase using pure water (50 ml2 times). Then, the aqueous phase was washed with toluene (50 ml3 times), and the solvent was removed by evaporation under reduced pressure to give a yellow oily substance. Sodium hydroxide (19.2 g, 480 mmol) was dissolved in pure water (20 ml), and the sodium hydroxide solution was gradually added to the obtained yellow oily substance, and the mixture was stirred for 12 hours. After that, distillation was performed to give 3-methylpyrrolidine (18.7 g, 219 mmol) which is a colorless transparent liquid. Into formic acid (21.6 g, 470 mmol) being water-cooled, 3-methylpyrrolidine (18.7 g, 219 mmol) was gradually added. Next, a 37% formaldehyde solution (26 ml, 330 mmol) was added to this solution. This solution was heated and refluxed at 100 C., was cooled back to room temperature after a bubble generation, and was stirred for about 30 minutes. Then, the solution was heated and refluxed again for one hour. The formic acid was neutralized with sodium hydroxide, and then the target substance was extracted with diethyl ether and dried using magnesium sulfate, and the solvent was removed by evaporation. Then, distillation was performed, whereby 1,3-dimethylpyrrolidine (13.3 g, 134 mmol) which is a colorless transparent liquid was obtained. Bromopropane (22.3 g, 182 mmol) was added to methylene chloride (10 ml) to which 1,3-dimethylpyrrolidine (12.0 g, 121 mmol) was added, and the mixture was heated and refluxed for 24 hours. The solvent was removed by evaporation, and the obtained white residue was recrystallized in ethanol and ethyl acetate and then dried under reduced pressure at 80 C. for 24 hours, whereby 1,3-dimethyl-1-propylpyrrolidinium bromide (13.9 g, 63.4 mmol) which is a white solid was obtained. In pure water, 1,3-dimethyl-1-propylpyrrolidinium bromide (5.30 g, 23.9 mmol) and lithium bis(trifluoromethanesulfonyl)amide (7.55 g, 26.3 mmol) were mixed and stirred, so that an ionic liquid which is insoluble in water was obtained immediately. After that, the obtained ionic liquid was extracated with methylene chloride and then washed with pure water six times. The solvent was removed by evaporation and dried in vacuum at 100 C., so that 1,3-dimethyl-1-propylpyrrolidinium bis(trifluoromethanesulfonyl)amide (9.37 g, 22.2 mmol) was obtained. The compound obtained through the above steps was identified as 1,3-dimethyl-1-propylpyrrolidinium bis(trifluoromethanesulfonyl)amide which is a target substance by using a nuclear magnetic resonance (NMR) and mass spectrometry. 1H NMR data of the obtained compound is shown below. 1H-NMR (CDCl3, 400 MHz, 298 K): delta=0.97-1.05 (3H), 1.15-1.21 (3H), 1.67-1.99 (3H), 2.28-2.48 (1H), 2.58-2.78 (1H), 2.94-3.08 (1H), 3.06, 3.13 (3H), 3.18-3.34 (2H), 3.47-3.87 (3H)

Reference： [1]Patent: US2012/308882,2012,A1

9
[ 34375-89-8 ]
[ 1597-32-6 ]
[ 1431773-84-0 ]

Yield	Reaction Conditions	Operation in experiment
89%	In water; at 205℃; for 0.5h;Microwave irradiation;	A suspension of <strong>[1597-32-6]6-fluoropyridin-2-amine</strong> (448 mg, 4 mmol) and 3-methylpyrrolidine (408 mg, 4.8 mmol) in water (0.5 mL) was heated to 205 C. in a microwave oven for 30 minutes. The reaction mixture was purified by chromatography (silica gel, 200-300 mesh, petroleum ether:ethyl acetate=5:1) to give 6-(3-methylcyclopentyl)pyridin-2-amine (630 mg, 89%) as a colorless oil. LC-MS: [M+H]+, 178.2, tR=1.080 min.
89%	In water; at 205℃; for 0.5h;Microwave irradiation;	A suspension of <strong>[1597-32-6]6-fluoropyridin-2-amine</strong> (448 mg, 4 mmol) and 3-methylpyrrolidine (408 mg, 4.8 mmol) in water (0.5 mL) was heated to 205 C in a microwave oven for 30 minutes. The reaction mixture was purified by chromatography (silica gel, 200 - 300 mesh, petroleum ether ethyl acetate = 5 : 1) to give 6-(3-methylcyclopentyl)pyridin-2-amine (630 mg, 89 %) as a colorless oil. LC-MS : [M+H]+, 178.2, tR = 1.080min.

Reference： [1]Patent: US2013/109661,2013,A1 .Location in patent: Paragraph 0357-0358
[2]Patent: WO2013/64445,2013,A1 .Location in patent: Page/Page column 86

10
[ 44565-27-7 ]
[ 34375-89-8 ]

Yield	Reaction Conditions	Operation in experiment
40.64 g		4-Amino-2-methyl-1-butanol expressed by Structural Formula (f3-1) (0.5 mol)and carbon tetrachloride (1.0 mol, 2 eq) were dissolved in methylene chloride (150 ml), triphenylphosphine (0.55 mol, 1.1 eq) was added thereto, and then the mixture was heated to reflux at 40 C for approximately 3 hours. After that, the intermediate is extracted with water three times and the water was removed by evaporation under reduced pressure. The residue was transferred to a container, 60 ml of water andsodium hydroxide (1.0 mol, 2 eq) were added to the residue, and stirring was performed overnight (15 to 20 hours). After separation into two layers was observed, NaCl was added and salting-out and distillation were performed, so that 3-methylpyrrolidine expressed by Structural Formula (f3-2) (40.64 g, 0.5 mol) was obtained.
18.7 g		First, at room temperature, under a nitrogen atmosphere,<strong>[44565-27-7]4-amino-2-methyl-1-butanol</strong> (24.8g, 240mmol) and carbon tetrachloride (111g,720mmol) were mixed and subsequently triphenylphosphine (69.2g, 264mmol) wasdissolved in dehydrated dichloromethane (150ml) and added. After stirring for 1to 1.5 hours at 40 , pure water (50ml) was added to the reaction solutionand stirred well, and then water phase and dichloromethane phase wereseparated. Further a yellow oily substance was extracted (50ml × 2 times) from dichloromethanephase with pure water. Then, after the aqueous phase was washed (50ml × 3times) with toluene, the solvent was distilled off under reduced pressure to obtaina yellow oily substance.[0162]Sodium hydroxide (19.2g, 480mmol) was dissolved in purewater (20ml), aqueous solution of sodium hydroxide was added in small portionsto the obtained yellow oily substance and stirred for 12 hours. Then, bydistillation a colorless transparent liquid; 3-methyl pyrrolidine (18.7g,219mmol) was obtained.

Reference： [1]Patent: WO2013/162040,2013,A1 .Location in patent: Paragraph 0279; 0280
[2]Patent: JP2015/178509,2015,A .Location in patent: Paragraph 0161; 0162

11
[ 34375-89-8 ]
[ 3939-12-6 ]
6-(3-methylpyrrolidin-1-yl)nicotinonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 8183 - 8191

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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. 34375-89-8 ] {[proInfo.proName]}

Quality Control of [ 34375-89-8 ]

Related Doc. of [ 34375-89-8 ]

Product Details of [ 34375-89-8 ]

Safety of [ 34375-89-8 ]

Application In Synthesis of [ 34375-89-8 ]

[ 34375-89-8 ] Synthesis Path-Downstream 1~11

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry