Bis(2-chloroethyl) ether → HCID 68736110, compound

HRID 1878630Notes

Reaction equation

HRID 1878630 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([NH2:17])([CH3:16])[CH3:15])=[CH:10][CH:9]=2)[CH:5]=[N:6][CH:7]=1.Cl[CH2:19][CH2:20][O:21][CH2:22][CH2:23]Cl>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([N:17]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)([CH3:15])[CH3:16])=[CH:10][CH:9]=2)[CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 8115Bis(2-chloroethyl) etherHCID 68934351HCID 68934351, compound2×

Product 1

HCID 68736110HCID 68736110, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-[4-(5-bromo-pyridin-3-yl)-phenyl]-1-methyl-ethylamine (Intermediate 229) (1 eq, 1.72 mmol, 500 mg), TEA (3.5 eq, 6.01 mmol, 608 mg), and 2-chloroethyl ether (Sigma-Aldrich, St. Louis, USA) (4 eq, 6.87 mmol, 0.8 ml) in DMF (10 ml) is heated using microwave radiation at 150° C. for 1 h. The mixture is concentrated under reduced pressure, then sat. aqueous NaHCO3 solution is added, followed by extraction with EtOAc. The organic layer is dried with MgSO4, filtered, and the solvents are removed in vacuo. Purification or the crude mixture by column chromatography (hexane/EtOAc) gives the title compound; [M+H]+=361/363.

Workup

  1. temperatureis heated
  2. customat 150° C.
  3. customfor 1 h
  4. concentrationThe mixture is concentrated under reduced pressure
  5. additionsat. aqueous NaHCO3 solution is added
  6. extractionfollowed by extraction with EtOAc
  7. dry with materialThe organic layer is dried with MgSO4
  8. filtrationfiltered
  9. customthe solvents are removed in vacuo
  10. customPurification

Sources & evidence

ORD record
ord-c6a6d857da004709a7d3fc7feb4d30e7
Source dataset
uspto-grants-2012_11
Patent number
US08314112B2

Reaction notes

Loading…