Ethylene Oxide → HCID 67896111, compound

HRID 1460443Notes

Reaction equation

HRID 1460443 reaction equation
[CH2:1]1O[CH2:2]1.[F:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[C:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:7][CH:6]=1.S(Cl)([Cl:27])=O>CO.C1(C)C=CC=CC=1>[ClH:27].[F:24][C:21]1[CH:20]=[CH:19][C:18]([C:11]([C:8]2[CH:9]=[CH:10][C:5]([F:4])=[CH:6][CH:7]=2)=[C:12]2[CH2:17][CH2:16][N:15]([CH2:1][CH2:2][Cl:27])[CH2:14][CH2:13]2)=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 6354Ethylene OxideHCID 24386Thionyl ChlorideHCID 27244364-(Bis(4-fluorophenyl)methylene)piperidine

Product 1

HCID 67896111HCID 67896111, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
-20 °C

Procedure

0.31 mol of ethylene oxide is dissolved in a solution of 0.28 mol of 4-[bis(4-fluorophenyl)methylene]piperidine (prepared according to the process described in U.S. Pat. No. 3,922,276) in one liter of anhydrous methanol at -10° C., and the reaction is completed by stirring for 15 hours at -20° C. and then for 3 hours at 45° C. The mixture is concentrated under vacuum. The product is purified by chromatography on 140 g of 230-400 mesh silica using a mixture of dichloromethane and methanol (95:5 V/V) as eluent. The oil obtained is solubilized in one liter of anhydrous toluene and 0.27 mol of thionyl chloride is then added. The mixture is brought to reflux for 30 min to complete the reaction. The mixture is cooled to 20° C. and the precipitate formed is filtered off. Yield: 90%

Workup

  1. customprepared
  2. customat -10° C.
  3. waitfor 3 hours at 45° C
  4. concentrationThe mixture is concentrated under vacuum
  5. customThe product is purified by chromatography on 140 g of 230-400 mesh silica using
  6. additiona mixture of dichloromethane and methanol (95:5 V/V) as eluent
  7. customThe oil obtained
  8. temperatureto reflux for 30 min
  9. customthe reaction
  10. temperatureThe mixture is cooled to 20° C.
  11. customthe precipitate formed
  12. filtrationis filtered off

Sources & evidence

ORD record
ord-98642249380246e09651f8f1cc8bbe60
Source dataset
uspto-grants-1991_12
Patent number
US05071847

Reaction notes

Loading…