Bis(2-chloroethyl) ether → HCID 10754897, compound

HRID 1614792Notes

Reaction equation

HRID 1614792 reaction equation
[H-].[Na+].[C:3]1([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:16]([O:19][CH2:20][CH2:21]Cl)[CH2:17][Cl:18]>C(OCCCC)CCC>[Cl:18][CH2:17][CH2:16][O:19][CH2:20][CH2:21][N:9]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 8115Bis(2-chloroethyl) etherHCID 11487DiphenylamineHCID 24758Sodium hydride

Product 1

HCID 10754897HCID 10754897, compound

Reagents, catalysts & solvents 1

HCID 8909Butyl etherSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of sodium hydride (0.70 g, 0.023 mol, 80% oil dispersion) and diphenylamine (3.4 g, 0.020 mol) in dry dibutylether (30 ml) was heated at reflux temperature for 1 h under an atmosphere of nitrogen. The reaction mixture was cooled to 50° C. and 2,2'-dichlorodiethylether (10 ml) was added and the mixture was heated at reflux temperature for 16 h. The reaction mixture was cooled, filtered and the volatile components were removed in vacuo leaving 4.6 g of crude 2-chloro-1-(2-(diphenylamino)ethoxy)ethane as an oil. This oil was dissolved in dry dibutylether (10 ml) and ethyl (R)-3-piperidinecarboxylate (3.7 g, 0.024 mol) and potassium carbonate (3.3 g, 0.024 mol) were added. The mixture was heated at reflux temperature for 2 h under an atmosphere of nitrogen and then stirred overnight at room temperature. Ethyl acetate (50 ml) was added, the mixture was filtered and the solvent was evaporated in vacuo. The residue was submitted to flash chromatography on silica gel (150 g) using a mixture of n-heptane and THF (4:1) as eluent. This provided 3.8 g (48% calculated from diphenylamine) of the title compound as an oil. TLC: rf=0.22 (SiO2 ; n-heptane/THF=7:3).

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 1 h under an atmosphere of nitrogen
  3. temperaturethe mixture was heated
  4. temperatureat reflux temperature for 16 h
  5. temperatureThe reaction mixture was cooled
  6. filtrationfiltered
  7. customthe volatile components were removed in vacuo

Sources & evidence

ORD record
ord-c1cf2b142833407990a700c46f6fe20e
Source dataset
uspto-grants-1993_03
Patent number
US05198451

Reaction notes

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