Water → HCID 43119952, compound

HRID 1740839Notes

Reaction equation

HRID 1740839 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH2:12]([CH:14]1[O:16][CH2:15]1)Cl.O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.[OH-].[Na+]>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH:14]2[CH2:15][O:16]2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

7

Reactant 3

HCID 962WaterHCID 7835EpichlorohydrinHCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 43119952HCID 43119952, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 3.1 g piperidine-4-carboxylic acid ethyl ester, 6.4 ml epichlorohydrin and 0.1 g tetrabutylammonium bromide in 15 ml toluene and 15 ml concentrated sodium hydroxide solution is stirred for 4 h at room temperature and subsequently admixed with 50 ml water. The organic phase is removed, the aqueous phase is shaken three times with 20 ml methylene chloride each time, the combined organic phases are dried over sodium sulfate and the solvent is removed in a vacuum. 2.1 g (rac)-1-oxiran-2-ylmethylpiperidine-4-carboxylic acid ethyl ester is obtained. m/e=213.

Workup

  1. customThe organic phase is removed
  2. stirringthe aqueous phase is shaken three times with 20 ml methylene chloride each time
  3. dry with materialthe combined organic phases are dried over sodium sulfate
  4. customthe solvent is removed in a vacuum

Sources & evidence

ORD record
ord-33e10679983c4e3181e3da1b9ad711df
Source dataset
uspto-grants-1999_10
Patent number
US05972947

Reaction notes

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