Reaction #7309

Reaction equation

4-methylpiperdine

triethylamine

methylchloroformate

water

→

product

4-Methyl-piperidine-1-carboxylic acid methyl ester

Solvents

methylene chloride

methylene chloride

Conditions

Workup

1. 1
   Temperaturethe mixture was cooled in an ice bath
2. 2
   Otherthe layers were separated
3. 3
   WashThe organic layer was washed with dilute HCl
4. 4
   DryingNaHCO3, and brine, and then the organic layer was dried over sodium sulfate
5. 5
   Otherthe solvent was removed in vacuo
6. 6
   workup.DISTILLATIONThe product was distilled at 90-93 C at ˜10 mm pressure

Procedure

To a three neck round bottom flask was added 360 g of 4-methylpiperdine, 470 mL of triethylamine, and 390 mL of methylene chloride and the mixture was cooled in an ice bath. To this mixture was added methylchloroformate (260 mL) in methylene chloride (215 mL) slowly to maintain a reaction temperature of 20 C or below. The reaction was stirred overnight, then 200 mL of water was added and the layers were separated. The organic layer was washed with dilute HCl, satd. NaHCO3, and brine, and then the organic layer was dried over sodium sulfate and the solvent was removed in vacuo. The product was distilled at 90-93 C at ˜10 mm pressure to provide 338 g of product.

Source