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[ CAS No. 167483-90-1 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 167483-90-1
Chemical Structure| 167483-90-1
Structure of 167483-90-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 167483-90-1 ]

CAS No. :167483-90-1 MDL No. :MFCD27991902
Formula : C21H24N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 336.43 Pubchem ID :-
Synonyms :

Safety of [ 167483-90-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H317 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 167483-90-1 ]

* 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 [ 167483-90-1 ]

[ 167483-90-1 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 501-53-1 ]
  • [ 69584-91-4 ]
  • [ 167483-90-1 ]
  • 2
  • [ 501-53-1 ]
  • [ 69584-91-4 ]
  • [ 121-44-8 ]
  • [ 167483-90-1 ]
YieldReaction ConditionsOperation in experiment
117 g (71%) In methanol; dichloromethane; EXAMPLE 4 1-Benzyloxycarbonyl-spiro(indoline-3,4'-piperidinium) hydrochloride A solution of 99 g (489 mmol) of 1'-methylspiro(indoline-3,4'-piperidine) (prepared according to Ong, H. H. et al, J. Med. Chem., 1983, 26, 981-986) in 1 L of CH2 Cl2 and 82 mL (539 mmol) of Et3 N was cooled to 0-5 C. with an ice bath and 77 mL (539 mmol) of benzyl chloroformate was added over 30 min keeping the reaction temperature below 10 C. After stirring for 2 h 19 mL (136 mmol) of Et3 N and 15 mL (105 mmol) of benzyl chloroformate were added since the reaction was incomplete and stirred for 2 h. At this time, additional 19 mL (136 mmol) of Et3 N and 15 mL (105 mmol) of benzyl chloroformate were added. After 1 h, when a TLC indicated a complete reaction, the solution was concentrated in vacuo and the residue was partitioned between ether and saturated NaHCO3. The layers were separated, the organic layer was washed with saturated NaHCO3 and brine, and dried over MgSO4. The filtrate was concentrated and the residue was chromatographed on 2 kg of silica gel using 1-5% MeOH/CH2 Cl2 to obtain 117 g (71%) of 1-benzyloxycarbonyl-1'-methylspiro(indoline-3,4'-piperidine) as a yellow oil. The yellow oil was dissolved in 800 mL of 1,2-dichloroethane and cooled in ice bath as 50 mL (463 mmol) of 1-chloroethyl chloroformate keeping the temperature below 10 C. The resulting solution was heated to reflux. Gas evolution was noticed when the reaction temperature reached 70-75 C. After 1 h the solution was cooled, concentrated to ca. 250 mL in vacuo and 700 mL of methanol was added. The mixture was refluxed for 1.5 h and gas evolution was observed. The reaction was cooled to room temperature and concentrated in vacuo to a wet solid. The solid was slurried with cold methanol, the solid was filtered, washed with cold methanol and dried. The filtrates and the washing were combined and concentrated to a brown foam. The brown foam and the filtered solid were suspended in CH2 Cl2, washed with 2.5 N NaOH and the CH2 Cl2 solution was dried.
117 g (71%) In methanol; dichloromethane; EXAMPLE 4 1-Benzyloxycarbonyl-spiro(indoline-3,4'-piperidinium)hydrochloride A solution of 99 g (489 mmol) of 1'-methylspiro(indoline-3,4'-piperidine) (prepared according to Ong, H. H. et al, J. Med. Chem., 1983, 26, 981-986) in 1 L of CH2 Cl2 and 82 mL (539 mmol) of Et3 N was cooled to 0-5 C. with an ice bath and 77 mL (539 mmol) of benzyl chloroformate was added over 30 min keeping the reaction temperature below 10 C. After stirring for 2 h 19 mL (136 mmol) of Et3 N and 15 mL (105 mmol) of benzyl chloroformate were added since the reaction was incomplete and stirred for 2 h. At this time, additional 19 mL (136 mmol) of Et3 N and 15 mL (105 mmol) of benzyl chloroformate were added. After 1 h, when a TLC indicated a complete reaction, the solution was concentrated in vacuo and the residue was partitioned between ether and saturated NaHCO3. The layers were separated, the organic layer was washed with saturated NaHCO3 and brine, and dried over MgSO4. The filtrate was concentrated and the residue was chromatographed on 2 kg of silica gel using 1-5% MeOH/CH2 Cl2 to obtain 117 g (71%) of 1-benzyloxycarbonyl-1'-methylspiro(indoline-3,4'-piperidine) as a yellow oil. The yellow oil was dissolved in 800 mL of 1,2-dichloroethane and cooled in ice bath as 50 mL (463 mmol) of 1-chloroethyl chloroformate keeping the temperature below 10 C. The resulting solution was heated to reflux. Gas evolution was noticed when the reaction temperature reached 70-75 C. After 1 h the solution was cooled, concentrated to ca. 250 mL in vacuo and 700 mL of methanol was added. The mixture was refluxed for 1.5 h and gas evolution was observed. The reaction was cooled to room temperature and concentrated in vacuo to a wet solid. The solid was slurried with cold methanol, the solid was filtered, washed with cold methanol and dried. The filtrates and the washing were combined and concentrated to a brown foam. The brown foam and the filtered solid were suspended in CH2 Cl2, washed with 2.5 N NaOH and the CH2 Cl2 solution was dried.
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