Thionyl Chloride → HCID 14652592, compound

HRID 477823Notes

Reaction equation

HRID 477823 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][CH2:15]O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:19])=O>C(Cl)(Cl)Cl>[Cl:19][CH2:15][CH2:14][CH:10]1[O:11][CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 146525912-(4-Benzylmorpholin-2-yl)ethan-1-ol

Product 1

HCID 14652592HCID 14652592, compoundYield 121.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 200 ml of toluene is added 58 g of a solution of 70% RDB in toluene and to the mixture is added dropwise a solution of 26.3 of ethyl 4-benzyl-2-morpholinylacetate in 50 ml of toluene below 10° C. Further, after ice-cooling for 30 minutes, the mixture is stirred at room temperature overnight. After to the reaction mixture is successively added 20 ml of acetone and 100 ml of water, the inorganic substance precipitated is filtered off. The toluene layer is separated from the filtrate and dried over anhydrous magnesium sulfate. The solvent is concentrated under reduced pressure and the residue is purified by chromatography on silica gel to give 10.1 g of 2-(4-benzyl-2-morpholinyl)ethanol. To a mixture of 2.21 g of 2-(4-benzyl-2-morpholinyl)ethanol in 30 ml of chloroform is added 2.30 g of thionyl chloride and the system refluxed for 2.5 hours. After completion of the reaction, the solvent is concentrated under reduced pressure and to the residue are added water and ether. After neutralizing with potassium carbonate, the ether layer is separated and dried over anhydrous magnesium sulfate. The solvent is concentrated under reduced pressure to give 2.90 g of 2-(2-chloroethyl)-4-benzylmorpholine as an oily substance.

Workup

  1. temperaturethe system refluxed for 2.5 hours
  2. customAfter completion of the reaction
  3. concentrationthe solvent is concentrated under reduced pressure and to the residue
  4. additionare added water and ether
  5. customthe ether layer is separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationThe solvent is concentrated under reduced pressure

Sources & evidence

ORD record
ord-0e20fc8ed4cc42f6a171e740b4d24daf
Source dataset
uspto-grants-1989_12
Patent number
US04889857

Reaction notes

Loading…