Water → 1-(ethoxycarbonylmethyl)-2-piperidone

HRID 1679242Notes

Reaction equation

HRID 1679242 reaction equation
[C:1]1(=[O:7])[NH:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH2:10]([O:12][C:13](=[O:16])[CH2:14]Br)[CH3:11].O>CN(C)C=O.C(Cl)Cl>[O:7]=[C:1]1[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:14][C:13]([O:12][CH2:10][CH3:11])=[O:16]

Participants

7

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 126652-PiperidoneHCID 24758Sodium hydride

Product 1

HCID 107500141-(ethoxycarbonylmethyl)-2-piperidone

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

9.9 parts of δ-valerolactam (purchased from Aldrich Chemical Co., Milwaukee, Wisc. 53233) were dissolved in 100 part of dimethylformamide. To this solution was added 4.8 parts of a 50% dispersion of sodium hydride in mineral oil (purchased from Callgary Chemical Company, Callgary, Pa.). The reaction mixture was stirred for a period of 30 minutes. To the above reaction mixture 16.7 parts of ethylbromoacetate was added dropwise keeping the temperature less than 25° C during the addition. After the addition was completed, the reaction was stirred at room temperature for an additional 30 minutes. The reaction mass was poured into 200 parts of water. The product was isolated by extraction from the aqueous solution with three successive 200-part portions of methylene chloride. The combined organic extracts of the product were dried with anhydrous sodium sulfate. The solution of the product was filtered and the solvent was removed by evaporation at a reduced pressure of 50-300 mm on a rotary evaporator. The crude product obtained was further purified by vacuum distillation at 115° -120° C at 1.5 mm; 8.2 parts of product were obtained.

Workup

  1. customthe temperature less than 25° C
  2. additionduring the addition
  3. additionAfter the addition
  4. stirringthe reaction was stirred at room temperature for an additional 30 minutes
  5. dry with materialThe combined organic extracts of the product were dried with anhydrous sodium sulfate
  6. filtrationThe solution of the product was filtered
  7. customthe solvent was removed by evaporation at a reduced pressure of 50-300 mm on a rotary evaporator

Sources & evidence

ORD record
ord-031502b4dac8484e8460f750022bf05b
Source dataset
uspto-grants-1978_03
Patent number
US04080192

Reaction notes

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