1-Chloroethyl chloroformate → HCID 22615490, compound

HRID 842725Notes

Reaction equation

HRID 842725 reaction equation
C[N:2]1[CH2:7][CH2:6][C:5]2([C:15]3[C:10](=[C:11]4[O:19][CH2:18][CH2:17][O:16][C:12]4=[CH:13][CH:14]=3)[C:9](=[O:20])[O:8]2)[CH2:4][CH2:3]1.ClC(OC(Cl)C)=O>ClCCCl>[CH2:18]1[CH2:17][O:16][C:12]2[C:11](=[C:10]3[C:15](=[CH:14][CH:13]=2)[C:5]2([CH2:6][CH2:7][NH:2][CH2:3][CH2:4]2)[O:8][C:9]3=[O:20])[O:19]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 22615486HCID 22615486, compound

Product 1

HCID 22615490HCID 22615490, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Into a 25 ml round bottom flask fitted with a nitrogen inlet, condenser, and a magnetic stirring bar were placed 1′-methyl-(4,5-ethylenedioxy)spiro(isobenzofuran-1(3H),4′-piperidin)-3-one (501 mg, 1.82 mmol) and 5.5 ml of 1,2-dichloroethane. The mixture was cooled to 0° before 1-chloroethyl chloroformate (0.8 ml, 7.28 mmol) was added slowly via a syringe. The mixture was then heated to reflux for 72 hours. The mixture was concentrated in vacuo and the residue taken up in 5.5 ml of methanol. This mixture was heated to reflux for 3 hours before concentration. This residue was diluted with water and made basic with concentrated ammonium hydroxide. The aqueous mixture was extracted with ethyl acetate. The organics were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was taken up in 2% methanol:ammonium hydroxide and chromatographed (100:10:1 methylene chloride:methanol:ammonium hydroxide) to give 203 mg of title product (43%).

Workup

  1. customInto a 25 ml round bottom flask fitted with a nitrogen inlet, condenser, and a magnetic stirring bar
  2. additionwas added slowly via a syringe
  3. temperatureThe mixture was then heated
  4. temperatureto reflux for 72 hours
  5. concentrationThe mixture was concentrated in vacuo
  6. temperatureThis mixture was heated
  7. temperatureto reflux for 3 hours before concentration
  8. additionThis residue was diluted with water
  9. extractionThe aqueous mixture was extracted with ethyl acetate
  10. washThe organics were washed with brine
  11. dry with materialdried over sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customammonium hydroxide and chromatographed (100:10:1 methylene chloride:methanol:ammonium hydroxide)

Sources & evidence

ORD record
ord-b497863e3f5b4394a038a98a5c4a8172
Source dataset
uspto-grants-2002_04
Patent number
US06376505B1

Reaction notes

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