[ CAS No. 19869-42-2 ] {[proInfo.proName]}

Name: 19869-42-2|1-Methylazepan-4-one hydrochloride|98%
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Quality Control of [ 19869-42-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 19869-42-2 ]

Product Details of [ 19869-42-2 ]

CAS No. :	19869-42-2	MDL No. :	MFCD07779465
Formula :	C₇H₁₄ClNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BHSJZGRGJYULPA-UHFFFAOYSA-N
M.W :	163.65	Pubchem ID :	10197846
Synonyms :

Safety of [ 19869-42-2 ]

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 [ 19869-42-2 ]

* 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 [ 19869-42-2 ]

[ 19869-42-2 ] Synthesis Path-Downstream 1~14

Yield	Reaction Conditions	Operation in experiment
		Example 1 A side stream of 245.3 g of ethyl 4-(2-carbethoxyethyl-methylamino)butyrate is charged evenly under nitrogen over a period of 2 hours into a solution of 123.4 g of potassium tert-butylate in 1.3 l of boiling xylene pumped round a loop reactor and the mixture is allowed to react for a further 0.5 hours. 750 ml of azeotrope is distilled off. The reaction mixture is hydrolyzed at 50° to 80° C. by rapid addition to a mixture of 300 ml of concentrated (37percent) hydrochloric acid and 500 g of crushed ice. The organic layer separated off is washed twice, each time with 150 ml of semi-concentrated hydrochloric acid. The combined aqueous extracts are heated for 2 hours under vigorous reflux and then evaporated to dryness in vacuo. The residue is dissolved in 700 ml of isopropanol, filtered off hot from the undissolved potassium chloride and crystallized at 0° to -5° C. The residue filtered off is dried to constant weight in vacuo at elevated temperature. A second fraction can be obtained by concentrating the mother liquor to a volume of approximately 100 ml. 141.6 g (86.6percent) of 1-methyl-perhydroazepin-4-one HCl is obtained. Melting point: 167° C. (decomposition)
		Example 4 90.0 kg of ethyl 4-(2-carbethoxyethylmethylamino)butyrate is charged evenly under nitrogen over a period of 2 to 3 hours at the top of the column into a solution of 50.0 kg of potassium tert-butylate in 400 ml of boiling xylene and the mixture is allowed to react for a further 1 to 1.5 hours. Approximately 160 l of azeotrope is distilled off. The reaction mixture is hydrolyzed at 50° to 80° C. by rapid addition to a mixture of 80 l of concentrated (37percent) hydrochloric acid and 100 g of crushed ice. The organic phase separated off is washed twice, each time with 50 l of semi-concentrated hydrochloric acid. The combined aqueous extracts are heated for 2 hours under vigorous reflux and then evaporated to dryness in vacuo. The residue is dissolved in 400 l of isopropanol, filtered off hot from the undissolved potassium chloride and crystallized at 0° to -5° C. The residue filtered off is dried to constant weight in vacuo at elevated temperature. 43.2 kg (72.0percent) of 1-methylperhydroazepin-4-one HCl is obtained. Melting point: 162°-165° C. (decomposition)
		Example 8 34.0 kg of ethyl 4-(2-carbethoxyethylmethylamino)butyrate dissolved in 400 l of xylene is charged evenly under nitrogen over a period of 2 to 3 hours into a suspension of 5.0 kg of sodium hydride (80percent in mineral oil) in 200 l of boiling xylene and allowed to react for a further 0.5 hours. Approximately 400 l of azeotrope is distilled off. The reaction mixture is hydrolyzed at 50° to 80° C. by rapid addition to a mixture of 35 l of concentrated (37percent) hydrochloric acid and 60 g of crushed ice. The organic layer separated off is washed twice, each time with 30 l of semi-concentrated hydrochloric acid. The combined aqueous extracts are heated for 2 hours under vigorous reflux and then evaporated to dryness in vacuo. The residue is dissolved in 100 l of isopropanol, filtered off hot from the undissolved potassium chloride and crystallized at 0° to -5° C. The residue filtered off is dried to constant weight in vacuo at elevated temperature. 11.7 kg (52.0percent) of 1-methyl-perhydroazepin-4-one HCl is obtained. Melting point: 162°-164° C.

Example 9 245.3 g of ethyl 4-(2-carbethoxyethylmethylamino)butyrate is charged evenly, under nitrogen, over a period of 1.75 hours into a solution of 39.0 g of sodium hydride (80percent in white mineral oil) and 75 ml of ethanol in 1.3 l of boiling xylene and allowed to react for a further 0.5 hours. Approximately 700 of azeotrope is distilled off. The reaction mixture is hydrolyzed at 80° to 100° C. by rapid addition to a mixture of 300 ml of concentrated (37percent) hydrochloric acid and 500 g of crushed ice. The organic layer separated off is washed twice, each time with 150 ml of semi-concentrated hydrochloric acid. The combined aqueous extracts are heated for 2 hours under vigorous reflux and then evaporated to dryness in vacuo. The residue is extracted hot from 600 ml of isopropanol and crystallized. The residue filtered off is dried to constant weight in vacuo at elevated temperature. A second crop of material can be obtained by concentrating the mother liquor to a volume of approximately 100 ml. 44.3 g (27.1percent) of 1-methyl-perhydroazepin-4-one HCl is obtained. Melting point: 159°-161° C. (decomposition)

2
[ 19869-42-2 ]
1-methylperhydroazepin-4-ol HCl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; sodium borohydrid; In water; isopropyl alcohol;	Example 7 100 ml of 1N sodium hydroxide solution is added to a solution of 18.9 g of sodium borohydride in 100 ml of water. A solution of 163.6 g of 1-methylperhydroazepin-4-one HCl in 100 ml of water is added dropwise at an internal temperature of 0° to 5° C. The mixture is stirred for 2 hours at 0° to 5° C. and then for 2 hours at room temperature. The pH is adjusted to 2 to 3 by addition of semi-concentrated hydrochloric acid. The mixture is evaporated to dryness in vacuo, the residue is taken up in 600 ml of isopropanol, the inorganic salts are separated off at 60° to 75° C. and the product is crystallized in an ice bath. The product is filtered and dried to constant weight in vacuo at elevated temperature. 149 g (90percent) of 1-methylperhydroazepin-4-ol HCl is obtained. Melting point: 156°-158° C.

Reference： [1]Patent: US5760221,1998,A

3
[ 19869-42-2 ]
1H-azepine, 4-hydrazinohexahydro-1-methyl, dihydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		208 g of benzoyl hydrazine (1.0 eq), 9.4 ml of water, and 174 g of potassium hydroxide 50percent (1.00 eq) were mixed. Then, a solution of 250 g of <strong>[19869-42-2]4H-azepine-4-one, hexahydro-1-methyl hydrochloride</strong> in 415 ml of water was added at room temperature. A solution of 43.35 g of sodium borohydride (0.75 eq.) in 312 ml of water was also added. Once the reaction was completed 1200 ml of ethyl acetate were added. A two layer solution was formed. After 20 minutes of stirring at room temperature, the organic layer was separated. The aqueous solution was extracted with 575 ml of ethyl acetate. The organic layers were combined and the solution was filtered off. Then, 204 g hydrochloric acid 36percent (1.3 eq) at room temperature were added. A two layer solution was formed. The outcome aqueous solution was diluted with 250 ml of water, it was heated at reflux temperature and distilled until the temperature of the mixture was over 100 °C. Then, 400 g of hydrochloric acid were added (36percent) (3 eq) and the mixture refluxed during 4 hours. The mixture was cooled down to 60 °C and 925 ml of xylene were added. The organic layer was separated and washed once with 465 ml of xylene at the same temperature. The aqueous phase was kept as a solution of 1H-azepine, 4-hydrazinohexahydro-1-methyl dihydrochloride.

Reference： [1]Patent: EP2072510,2009,A1 .Location in patent: Page/Page column 5

4
[ 14150-94-8 ]
[ 19869-42-2 ]
[ 1027949-84-3 ]
[ 1027176-67-5 ]

Reference： [1]Synthesis,2010,p. 1339 - 1343

5
[ 1073-70-7 ]
[ 19869-42-2 ]
[ 1225434-00-3 ]

Yield	Reaction Conditions	Operation in experiment
78%		Example 1 Preparation of 9-chloro-l,2,3,4,5,6-hexahvdro-3-methylazepmor4,5-b1mdole[0366] The title compound was prepared by following general procedure 1 1-Methylazepan- 4-one hydrochloride (164 mg, 1 mmol) and 4-chlorophenylhydrazme hydrochloride (179 mg, 1 mmol) were heated in a mixture of 7percent sulfuric acid in 1,4-dioxane (2-3 mL) overnight under nitrogen Two liquid layers persisted throughout the reaction The mixture was poured on to ice and basified with 50percent aq NaOH The resulting precipitate was filtered, washed well with water, and dried in air to give 9-chloro-l,2,3,4,5,6-hexahydro-3-methylazepmo[4,5-b]mdole as a dark brown solid (183 mg 78percent yield)

Reference： [1]Patent: WO2010/51503,2010,A1 .Location in patent: Page/Page column 247

6
[ 637-60-5 ]
[ 19869-42-2 ]
[ 20779-57-1 ]

Yield	Reaction Conditions	Operation in experiment
		Example 2 Preparation of 1.2.3.4.5.6-hexahvdro-3.9-dimethylazepmor4.5-b1mdole[0367] The title compound was prepared by following general procedure 1 p-Tolyl hydrazine hydrochloride (15 g, 94 55 mmol) was taken into 7percent H2SO4 in 1,4-dioxane (650 mL), 1- methylazepan-4-one HCl (15 4 g, 94 55 mmol) was added and stirred at RT for 10 mm The reaction mixture was stirred at 800C for 14 h After completion of the reaction, reaction mass was slowly basified with 50percent NaOH solution, extracted with ethyl acetate The organic layer was dried over anhydrous sodium sulfate and evaporated to dryness and purified by column chromatography (silica gel 100-200 mesh, eluent 10percent methanol-DCM) to afford 3,9-dimethyl- l,2,3,4,5,6-hexahydroazepmo[4,5-b]mdole (5 g)

Reference： [1]Patent: WO2010/51503,2010,A1 .Location in patent: Page/Page column 247

7
[ 555-16-8 ]
[ 19869-42-2 ]
[ 1431280-08-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; In acetic acid; at 20℃;	(3E,5E)-l-methyl-3,5-bis[(4-nitrophenyl)methylidene]azepan-4-one (compound No. 1563). N-methylazepan-4-one HCI (50 mg, 0.30 mmol) and 4-nitrobenzaldehyde were dissolved in acetic acid (5 mL) and stirred for 10 min, then cone. H2S04 (50 mu?) was added slowly and the mixture was stirred at rt overnight. More concentrated H2S04 (100 mu?) was added and stirring was continued at rt for 6 h. Additional 500 mu? of concentrated H2S04 was added and the reaction stirred overnight. A further 350 mu? of cone. H2S04 was added and stirring continued for additional 5 h, during which period further H2S04 was added in two portions (500 mu? and 250 mu?). Then water ( 3 x reaction volume) was added and the mixture was stirred until rt was reached. The reaction mixture was extracted with ethyl acetate (3 x reaction volume). The phases were separated and the organic phase concentrated to yield a dark yellow viscous oil. The crude product was purified by preparative HPLC, (XBridge column; eluents 50 mM ammonium carbonate buffer at pH 10 and methanol) giving the title product as a yellow solid (26.3 mg). LCMS System A: Rt 1.87 m/z [M+H]+ 394.1, System B: Rt 2.57.

Reference： [1]Patent: WO2013/58691,2013,A1 .Location in patent: Page/Page column 22

8
[ 104-88-1 ]
[ 19869-42-2 ]
C₂₁H₁₉ClN₂O₃ [ No CAS ]

Reference： [1]Patent: WO2013/58691,2013,A1

9
[ 104-88-1 ]
[ 19869-42-2 ]
C₁₄H₁₆ClNO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; In acetic acid; at 20℃; for 192.0h;	(3E,5E)-5-[(4-chlorophenyl)methylidene]-3-[(4-nitrophenyl)methylidene]azepan-4-one (compound No. 1583). <strong>[19869-42-2]N-methylazepan-4-one hydrochloride</strong> (75 mg, 0.46 mmol) and4-chlorobenzaldehyde (64 mg, 0.46 mmol) were dissolved in acetic acid (7 mL) and stirred for 10 min, then cone. H2S04 (350 mu?) was added slowly and the mixture was stirred at rt for 8 days. More cone. H2S04 was added during days 2-4 (0.175 mL, 0.35 mL, 0.25 mL respectively). Water (2 x reaction volume) was added and the solution extracted with ethyl acetate (2 x reaction volume). The organic phase was concentrated to give Intermediate 8. A portion of the intermediate (35 mg, 0.14 mmol) and 4-nitrobenzaldehyde (69.5 mg, 0.46 mmol) were dissolved in acetic acid (2.5 mL) and stirred for 10 min, then cone. H2S04 (200 mu?) was added slowly and the mixture was stirred at rt for 5 days. More cone. H2S04 (0.2 mL) was added, and stirring continued for 5 more days. Water (2 x reaction volume) was added and the solution extracted with ethyl acetate (2 x reaction volume). The organic phase was concentrated and the residue purified by preparative LC to give the title compound (1.8 mg) as a yellow solid of 94percent purity. LCMS System A: Rt 1.98/2.04 m/z[M+H]+ 383.1, System B: Rt 2.82/2.98.

Reference： [1]Patent: WO2013/58691,2013,A1 .Location in patent: Page/Page column 24

10
[ 459-57-4 ]
[ 19869-42-2 ]
[ 1431280-15-7 ]

Reference： [1]Patent: WO2013/58691,2013,A1

11
[ 459-57-4 ]
[ 19869-42-2 ]
C₁₄H₁₆FNO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; In acetic acid; at 20℃;	(3E,5E)-5-[(4-fluorophenyl)methylidene]-3-[(4-methoxyphenyl)methylidene]-l- methylazepan-4-one (compound No. 1577). <strong>[19869-42-2]N-methylazepan-4-one hydrochloride</strong> (75 mg, 0.46 mmol) and 4-fluorobenzaldehyde were dissolved in acetic acid (7 mL) and stirred for 10 min, then cone. H2S04 (350 iL) was added slowly and the mixture was stirred at rt for 8 days. More cone. H2S04 was added during days 2-4 (0.175 mL, 0.35 mL, 0.25 mL respectively). Water was added and the solution extracted with ethyl acetate (twice the volume of reaction mixture). The organic phase was concentrated to give Intermediate 5. A portion of this intermediate (35 mg, 0.15 mmol) and 4-methoxybenzaldehyde (17 mu?, 0.15 mmol) were dissolved in acetic acid (2.5 mL) and stirred for 10 min, then cone. H2S04 (0.20 mL) was added slowly and the reaction stirred for five days. Water (2 x reation volume) was added and the reaction mixture extracted with ethyl acetate (2 x reaction volume). The organic layer was concentrated and water was added. A precipitate was formed and filtered off to give the title product (11.2 mg) in 91percent purity as a yellow solid. LCMS System A: Rt 1.86 m/z [M+H]+ 352.1, System B: Rt 2.79.

Reference： [1]Patent: WO2013/58691,2013,A1 .Location in patent: Page/Page column 23

12
[ 1119-48-8 ]
[ 19869-42-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: thionyl chloride / 4 h / -5 - 0 °C / Large scale 2: triethylamine / methanol / 25 °C 3: potassium <i>tert</i>-butylate / 5,5-dimethyl-1,3-cyclohexadiene / Reflux

Reference： [1]Current Patent Assignee: SICHUAN D INNOVATION PHARMACEUTICAL - CN112079739, 2020, A

13
[ 19869-42-2 ]
[ 613-94-5 ]
[ 110406-94-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: methanol / 2 h / 20 - 30 °C 1.2: 2 h / 20 °C 2.1: potassium borohydrate / methanol; lithium hydroxide monohydrate / 3 h / 10 - 55 °C

Reference： [1]Current Patent Assignee: KUNMING YUANRUI PHARMACEUTICAL - CN113956239, 2022, A

14
[ 19869-42-2 ]
[ 613-94-5 ]
[ 53242-76-5 ]
[ 58581-89-8 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1-methylazepan-4-one hydrochloride; benzoic acid hydrazide at 20℃; Stage #2: With potassium hydroxide In methanol at 0 - 20℃; for 5h; Stage #3: 2-(p-chlorophenylacetyl)benzoic acid Further stages;	7 Example 7: Preparation of Azelastine Hydrochloride Add 1 mol of N-methylhexahydroazepin-4-one hydrochloride and 1.1 mol of benzoic hydrazide to the reaction kettle, and stir the reaction at room temperature for 1-5 h.Then cool with ice-salt water or ice-salt bath until0-20; add 500mL of methanol solution of 2mol/L KOH dropwise for 5h,Add 1.30 mol of potassium borohydride, continue to cool and stir for 30 min, and then stir for 6 h at 40-50 °C;Then use DCM (extraction (10ml×3), after drying with 0.50kg MgSO4, then add HCl-containing ether solution to form salt, and precipitation;Then add 10kg pure water and 1 mol of 2-(p-chlorophenylacetyl) benzoic acid, adjust the pH to 7 with 20% NaOH solution, stir and reflux, and cool under stirring to make the oily matter become solid particles, use 20% The pH of the NaOH was adjusted to 9, so that the azelastine free base was fully separated out, left standing, filtered, washed with water and dried;The dried 4-(4-chlorobenzyl)-2-(hexahydro-1-methyl-IH-azepin-4-yl)-1-(2H)-phthalazine was first dissolved by heating with acetone, added Activated carbon, stirred and refluxed for 60min, filtered while hot, the filter residue was washed with hot acetone, the filtrate was salted with HCl-containing isopropanol solution under cooling and stirring, frozen, filtered, washed with cold acetone, drained, and dried at 100°C Dry, and recrystallize once more from acetone and ethanol to give 4-(4-chlorobenzyl)-2-(hexahydro-1-methyl-IH-azepin-4-yl)-1-(2H)- Phthalazine hydrochloride (99.1%).

Reference： [1]Current Patent Assignee: GOOD DOCTOR PHARMACEUTICAL GROUP LTD - CN114507184, 2022, A Location in patent: Paragraph 0047-0048

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P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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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. 19869-42-2 ] {[proInfo.proName]}

Quality Control of [ 19869-42-2 ]

Related Doc. of [ 19869-42-2 ]

Product Details of [ 19869-42-2 ]

Safety of [ 19869-42-2 ]

Application In Synthesis of [ 19869-42-2 ]

[ 19869-42-2 ] Synthesis Path-Downstream 1~14

Similar Product of [ 19869-42-2 ]

Related Functional Groups of [ 19869-42-2 ]

Ketones

Related Parent Nucleus of [ 19869-42-2 ]

Other Aliphatic Heterocycles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Similar Product of
[ 19869-42-2 ]

Related Functional Groups of
[ 19869-42-2 ]

Related Parent Nucleus of
[ 19869-42-2 ]