Structure of 77801-91-3
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 77801-91-3 |
Formula : | C9H8ClN |
M.W : | 165.62 |
SMILES Code : | CN1C=CC2=C1C=CC=C2Cl |
MDL No. : | MFCD13178459 |
InChI Key : | WUFPOENCCOPNCC-UHFFFAOYSA-N |
Pubchem ID : | 13048759 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H302 |
Precautionary Statements: | P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; ammonium chloride; magnesium; In tetrahydrofuran; dichloromethane; ethyl acetate; | STEP B 1-benzyl-3-[1-methyl-1H-indol-4-yl]-3-piperidinol hydrochloride A mixture of 12 g of magnesium in 155 ml of tetrahydrofuran was refluxed while a solution of 38 g of 1-methyl-4-chloro-1H-indole, 4.5 ml of 1,2-dibromoethane and 115 ml of tetrahydrofuran was slowly added thereto. After the addition of a few drops of methyl iodide, the mixture was refluxed for 6 hours and was then cooled to 45 C. to form a solution to which a solution of 1-benzyl-3-piperidone (prepared from 50 g of <strong>[50606-58-1]1-benzyl-3-piperidone hydrochloride</strong>) in 115 ml of tetrahydrofuran was added dropwise. The mixture was refluxed for 2 hours and then allowed to cool to room temperature. The mixture was stirred for 16 hours and was then cooled in an ice bath while 200 ml of an aqueous saturated ammonium chloride solution was added dropwise thereto. The mixture was filtered and the filter was rinsed with water and ethyl acetate. The decanted aqueous phase was extracted with ethyl acetate and the organic phase was washed with aqueous sodium chloride solution and was evaporated to dryness under reduced pressure. The residue was taken up in ether and the solution was extracted with 1 N hydrochloric acid. The aqueous phase was made alkaline and was extracted with ethyl acetate. The organic phase was evaporated to dryness under reduced pressure and the 73.4 g of residue were chromatographed over silica gel. Elution with a 9-1 cyclohexane-triethylamine mixture yielded a product which was taken up in methylene chloride. The solution was filtered and the filtrate was evaporated to dryness under reduced pressure to obtain 60.5 g of 1-benzyl-3-[1-methyl-1H-indol-4-yl]-3-piperidinol. The said base was dissolved in 300 ml of ethyl acetate and a solution of hydrogen chloride in ethyl acetate was added to the solution dropwise until the pH was 4. The mixture was iced for 16 hours and was vacuum filtered and the recovered product was washed with ethyl acetate and dried at 50 C. under reduced pressure to obtain 59.6 g of 1-benzyl-3-[1-methyl-1H-indol-4-yl]-3-piperidinol hydrochloride melting at 250 C. Analysis: C21 H25 N2 O: molecular weight=356.90. Calculated: %C 70.67; %H 7.06; %N 7.85; %Cl 9.93. Found: %C 70.4; %H 6.9; %N 7.9; %Cl 10.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; sodium chloride; ammonium chloride; magnesium; In tetrahydrofuran; dichloromethane; ethyl acetate; | STEP B 3-[1-methyl-1H-indole-4-yl]-1-benzyl-3-piperidinol hydrochloride 12 g of magnesium were introduced into 155 ml of tetrahydrofuran and the mixture was refluxed. A solution of 38 g of 1-methyl-4-chloro-1H-indole and 4.5 ml of 1,2-dibromomethane in 115 ml of tetrahydrofuran was slowly introduced after initiation with a few drops of methyl iodide and the reflux was maintained for 6 hours. The mixture was then cooled to 45 C. to obtain a solution of the magnesium derivative which was used as is. A solution of N-benzyl-3-piperidone prepared from 50 g of N-benzyl-3-piperidone hydrochloride in 115 ml of tetrahydrofuran was introduced dropwise into the solution obtained above and the mixture was heated for 2 hours at reflux, allowed to cool and stirred for 16 hours in an ice bath. 200 ml of saturated ammonium chloride solution were added dropwise and the mixture was filtered. The filter was rinsed with water and with ethyl acetate and the decanted aqueous phase was extracted again with ethyl acetate. The organic phase was washed with a saturated aqueous solution of sodium chloride and was distilled to dryness under reduced pressure. The residue was taken up in ether and the solution was extracted with N hydrochloric acid, made alkaline, re-extracted with ethyl acetate and distilled to dryness under reduced pressure to obtain 73.4 g of crude product. The residue was purified by chromatography over a column of silica and elution with a 9-1 cyclohexane-triethylamine mixture. The product was taken up in methylene chloride and the solution was filtered and distilled to dryness under reduced pressure to obtain 60.5 g of the desired base. The said base was dissolved in 300 ml of ethyl acetate and a solution of hydrochloric acid in ethyl acetate was added dropwise until the pH was 4. The mixture was chilled for 16 hours and filtered and the recovered product was washed with ethyl acetate and dried at 50 C. under vacuum to obtain 59.6 g of 3-[1-methyl-1H-indole-4-yl]-1-benzyl-3-piperidinol hydrochloride melting at 250 C. |
Tags: 77801-91-3 synthesis path| 77801-91-3 SDS| 77801-91-3 COA| 77801-91-3 purity| 77801-91-3 application| 77801-91-3 NMR| 77801-91-3 COA| 77801-91-3 structure
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
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Code | Phrase |
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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 |
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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: |
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P321 | |
P322 | |
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P337 | If eye irritation persists: |
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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. |
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P371 | In case of major fire and large quantities: |
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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 |
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P402 | Store in a dry place. |
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P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
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P410 | Protect from sunlight. |
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P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
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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 | |
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P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
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H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
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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 |
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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 |
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