Ethyl chloroformate → Ethyl 4-acetamidopiperidine-1-carboxylate

HRID 1017548Notes

Reaction equation

HRID 1017548 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-61fbb833083e4e3aa2a632c22d4d75b2
Source dataset
uspto-grants-2002_11
Patent number
US06479501B2

Reaction notes

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