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COC(=O)C1=CCCNC1Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | methyl 1,2,3,6-tetrahydropyridine-5-carboxylate |
|---|---|
| IUPAC Name | — |
| CAS Number | 495-19-2 |
| Database ID | 160492 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
methyl 1,2,3,6-tetrahydropyridine-5-carboxylate (CAS 495-19-2) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 160492
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-446fb1b31dd24c35aa9d33d0d5f603faConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-cc7936604f2c4c13b0ff47b623973925Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-c92ab13fe95f4de580d9c9bb405ace48Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-0ab3db67f5f84bd692fda42733bd09a8Conditions: temp:-15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Arecoline (39.5 g, 0.25 mol) was dissolved in dry toluene (20 ml). 1-Chloroethyl chloroformate (30.5 ml) was added slowly at 0-5° C. The mixture was heated at 80° C. for 2 h, cooled to room temperature, filtered and evaporated to dryness in vacuo. The residue was dissolved in methylene chloride (400 ml) and extracted with 10% aqueous sodium carbonate. The organic layer was dried over magnesium sulfate, filtered and evaporated to dryness to give methyl 1,2,5,6-tetrahydropyridine-3-carboxylate (Yield: 30.5 g, 85%). Methyl 1,2,5,6-tetrahydropyridine-3-carboxylate (1.1 g, 7.8 mmol) was dissolved in methylene chloride (20 ml) and cooled to -15° C. Triethyl amine (2.2 ml, 15,8 mmol) and a solution of benzyl chloroformate (1.2 ml, 8,4 mmol) in methylene chloride (10 ml) were added. Stirring at room temperature for 1.5 h followed by evaporation to dryness. The residue was dissolved in methylene chloride and extracted with water two times. The organic layer separated, dried and evaporated to dryness in vacuo to give methyl 1-benzyloxycarbonyl-1,2,5,6-tetrahydropyridine-3-carboxylate as an oil (Yield: 2.0 g, 92%). followed by evaporation to dryness The residue was dissolved in methylene chloride extracted with water two times The organic layer separated dried evaporated to dryness in vacuo
Source ID: ord-e6c5a213837f49e0a9ee6917641ff2e9Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Arecoline (39.5 g, 0.25 mol) was dissolved in dry toluene (20 ml). 1-Chloroethyl chloroformate (30.5 ml) was added slowly at 0-5° C. The mixture was heated at 80° C. for 2 h, cooled to room temperature, filtered and evaporated to dryness in vacuo. The residue was dissolved in methylene chloride (400 ml) and extracted with 10% aqueous sodium carbonate. The organic layer was dried over magnesium sulfate, filtered and evaporated to dryness to give methyl 1,2,5,6-tetrahydropyridine-3-carboxylate (Yield: 30.5 g, 85%). Methyl 1,2,5,6-tetrahydropyridine-3-carboxylate (1.1 g, 7.8 mmol) was dissolved in methylene chloride (20 ml) and cooled to -15° C. Triethyl amine (2.2 ml, 15,8 mmol) and a solution of benzyl chloroformate (1.2 ml, 8,4 mmol) in methylene chloride (10 ml) were added. Stirring at room temperature for 1.5 h followed by evaporation to dryness. The residue was dissolved in methylene chloride and extracted with water two times. The organic layer separated, dried and evaporated to dryness in vacuo to give methyl 1-benzyloxycarbonyl-1,2,5,6-tetrahydropyridine-3-carboxylate as an oil (Yield: 2.0 g, 92%). cooled to room temperature filtered evaporated to dryness in vacuo The residue was dissolved in methylene chloride (400 ml) extracted with 10% aqueous sodium carbonate The organic layer was dried over magnesium sulfate filtered evaporated to dryness
Source ID: ord-e9c18a0b1a7b408296d154d0f18b1cdaConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-446fb1b31dd24c35aa9d33d0d5f603faConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-cc7936604f2c4c13b0ff47b623973925Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-c92ab13fe95f4de580d9c9bb405ace48Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-0ab3db67f5f84bd692fda42733bd09a8Conditions: temp:-15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Arecoline (39.5 g, 0.25 mol) was dissolved in dry toluene (20 ml). 1-Chloroethyl chloroformate (30.5 ml) was added slowly at 0-5° C. The mixture was heated at 80° C. for 2 h, cooled to room temperature, filtered and evaporated to dryness in vacuo. The residue was dissolved in methylene chloride (400 ml) and extracted with 10% aqueous sodium carbonate. The organic layer was dried over magnesium sulfate, filtered and evaporated to dryness to give methyl 1,2,5,6-tetrahydropyridine-3-carboxylate (Yield: 30.5 g, 85%). Methyl 1,2,5,6-tetrahydropyridine-3-carboxylate (1.1 g, 7.8 mmol) was dissolved in methylene chloride (20 ml) and cooled to -15° C. Triethyl amine (2.2 ml, 15,8 mmol) and a solution of benzyl chloroformate (1.2 ml, 8,4 mmol) in methylene chloride (10 ml) were added. Stirring at room temperature for 1.5 h followed by evaporation to dryness. The residue was dissolved in methylene chloride and extracted with water two times. The organic layer separated, dried and evaporated to dryness in vacuo to give methyl 1-benzyloxycarbonyl-1,2,5,6-tetrahydropyridine-3-carboxylate as an oil (Yield: 2.0 g, 92%). followed by evaporation to dryness The residue was dissolved in methylene chloride extracted with water two times The organic layer separated dried evaporated to dryness in vacuo
Source ID: ord-e6c5a213837f49e0a9ee6917641ff2e9Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Arecoline (39.5 g, 0.25 mol) was dissolved in dry toluene (20 ml). 1-Chloroethyl chloroformate (30.5 ml) was added slowly at 0-5° C. The mixture was heated at 80° C. for 2 h, cooled to room temperature, filtered and evaporated to dryness in vacuo. The residue was dissolved in methylene chloride (400 ml) and extracted with 10% aqueous sodium carbonate. The organic layer was dried over magnesium sulfate, filtered and evaporated to dryness to give methyl 1,2,5,6-tetrahydropyridine-3-carboxylate (Yield: 30.5 g, 85%). Methyl 1,2,5,6-tetrahydropyridine-3-carboxylate (1.1 g, 7.8 mmol) was dissolved in methylene chloride (20 ml) and cooled to -15° C. Triethyl amine (2.2 ml, 15,8 mmol) and a solution of benzyl chloroformate (1.2 ml, 8,4 mmol) in methylene chloride (10 ml) were added. Stirring at room temperature for 1.5 h followed by evaporation to dryness. The residue was dissolved in methylene chloride and extracted with water two times. The organic layer separated, dried and evaporated to dryness in vacuo to give methyl 1-benzyloxycarbonyl-1,2,5,6-tetrahydropyridine-3-carboxylate as an oil (Yield: 2.0 g, 92%). cooled to room temperature filtered evaporated to dryness in vacuo The residue was dissolved in methylene chloride (400 ml) extracted with 10% aqueous sodium carbonate The organic layer was dried over magnesium sulfate filtered evaporated to dryness
Source ID: ord-e9c18a0b1a7b408296d154d0f18b1cdaPubChem References
These sources are listed in the compound's public database record.
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