Ethyl chloroformate → Ethyl 4-acetamidopiperidine-1-carboxylate

HRID 1976826Notes

Reaction equation

HRID 1976826 reaction equation
[C:1]([NH:4][CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)(=[O:3])[CH3:2].C(=O)(O)[O-].[Na+].Cl[C:17]([O:19][CH2:20][CH3:21])=[O:18]>O.C(OCC)(=O)C>[C:1]([NH:4][CH:5]1[CH2:10][CH2:9][N:8]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 516892Sodium BicarbonateHCID 14451564-Acetamidopiperidine

Product 1

HCID 18403966Ethyl 4-acetamidopiperidine-1-carboxylateYield 103.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-acetamidopiperidine (20.7 g), sodium bicarbonate (10.6 g) and water (300 ml) was cooled to 0° C., and 17.7 g of ethyl chloroformate was added dropwise, with stirring. Upon completion of the addition, the reaction mixture was allowed to warm to ambient temperature and was diluted with water and ethyl acetate. The layers were separated, and the organic layer was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated to give 32.2 g (100%) of product.

Workup

  1. additionUpon completion of the addition
  2. customThe layers were separated
  3. washthe organic layer was washed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-5655b5b754ed4f648f9e139fb88fe57d
Source dataset
uspto-grants-2001_05
Patent number
US06229014B1

Reaction notes

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