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Chemical Structure| 41467-01-0 Chemical Structure| 41467-01-0

Structure of 41467-01-0

Chemical Structure| 41467-01-0

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Product Details of [ 41467-01-0 ]

CAS No. :41467-01-0
Formula : C7H13NO
M.W : 127.18
SMILES Code : O=CC1N(C)CCCC1
MDL No. :MFCD09744984

Safety of [ 41467-01-0 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H226-H302-H315-H318-H335
Precautionary Statements:P210-P233-P240-P241-P242-P243-P261-P264-P270-P271-P280-P301+P312+P330-P303+P361+P353-P304+P340+P312-P305+P351+P338+P310-P332+P313-P370+P378-P403+P233-P403+P235-P405-P501
Class:3
UN#:1993
Packing Group:

Application In Synthesis of [ 41467-01-0 ]

* 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 [ 41467-01-0 ]

[ 41467-01-0 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 20845-34-5 ]
  • [ 41467-01-0 ]
YieldReaction ConditionsOperation in experiment
31% Step 11-Methylpiperidine-2-carbaldehydeDimethyl sulfoxide (3.3 mL, 46 mmol) was dissolved in 15 mL of dichloromethane in a dry ice bath, followed by dropwise slowly addition of oxalyl chloride (2.6 mL, 31 mmol).After stirring for 45 minutes, a solution of (1-methyl-2-piperidyl)methanol 6a (1 g, 7.74 mmol) in 5 mL of dichloromethane was added dropwise to the solution.The reaction mixture was stirred for 45 minutes, then added with triethylamine (7.2 mL, 52 mmol), and stirred for 10 minutes, then warmed up to room temperature and stirred for 1 hour.The reaction mixture was washed with water (20 mL) and saturated brine (20 mL) successively.The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure then the resulting residue was purified by alkaline alumina column chromatography with elution system A to obtain the title compound 1-methylpiperidine-2-carbaldehyde 6b (300 mg, yield 31.0percent) as a brown oil, which was directly used in the next step without purification.
DMSO (122 mg, 1.56 mmol) in DCM (0.5 mL) was cooled to -78°C, and trifluoroacetic acid anhydride (246 mg, 1.17 mmol) in DCM (0.5 mL) was added slowly. The mixture was stirred at -78°C for 45 min. Subsequently, a solution of (l-methylpiperidin-2-yl)methanol (101 mg, 0.78 mmol) in DCM (1.0 mL) was added dropwise, and the mixture was kept at -78°C for 1 h. Triethyl- amine (99 mg, 0.98 mmol) was added, and the mixture was slowly warmed to rt. The mixture was then diluted with tert-butyl methyl ether/DCM (1 :1) and extracted with 1 N hydrochloric acid. The aqueous phase was washed twice with tert-butyl methyl ether, then basifed with sodium carbonate <n="153"/>solution and extracted with tert-butyl methyl ether. The organic phase was dried over sodium sulfate, and the solvent was carefully removed in vacuo. The residue was dissolved in THF (1.0 mL) to give solution A.
Under dry ice bath, dimethylsulfoxide (3.3 mL, 46 mmol) was dissolved in 15 mL of methylene chloride. It was slowly added dropwise oxalyl chloride (2.6 mL, 31 mmol). The reaction was stirred for 45 minutes. Add dropwise 5 mL (1-methyl-2-piperidine)methanol 6a (1 g, 7.74 mmol) in methylene chloride. The reaction was continued for 45 minutes. Add triethylamine (7.2 mL, 52 mmol). The reaction was stirred for 10 minutes. At room temperature react for one hour. The reaction mixture was washed successively with water (20 mL) and washed with saturated sodium chloride solution (20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure, column chromatography using basic alumina A to the resulting residue was purified eluent system to give the title product, 1-methyl - piperidin-2-carbaldehyde 6b (300 mg, brown liquid), yield: 31.0percent, crude without purification directly to the next reaction.
 

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