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Chemical Structure| 77801-91-3 Chemical Structure| 77801-91-3

Structure of 77801-91-3

Chemical Structure| 77801-91-3

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Product Details of [ 77801-91-3 ]

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

Safety of [ 77801-91-3 ]

GHS Pictogram:
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

Application In Synthesis of [ 77801-91-3 ]

* 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 [ 77801-91-3 ]

[ 77801-91-3 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 77801-91-3 ]
  • [ 40114-49-6 ]
  • [ 50606-58-1 ]
  • [ 106-93-4 ]
  • 1-benzyl-3-[1-methyl-1H-indol-4-yl]-3-piperidinol hydrochloride [ No CAS ]
YieldReaction ConditionsOperation 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.
  • 2
  • 1,2-dibromomethane [ No CAS ]
  • [ 77801-91-3 ]
  • [ 50606-58-1 ]
  • 1-benzyl-3-[1-methyl-1H-indol-4-yl]-3-piperidinol hydrochloride [ No CAS ]
YieldReaction ConditionsOperation 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.
 

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