1-Chloroethyl chloroformate → HCID 69217200, compound

HRID 747837Notes

Reaction equation

HRID 747837 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([C:11]23[CH2:30][CH:15]([CH2:16][CH:17]([N:19]4[C:27](=[O:28])[C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[C:20]4=[O:29])[CH2:18]2)[N:14](C)[CH2:13][CH:12]3[CH3:32])[CH:8]=[CH:9][CH:10]=1)([CH3:3])[CH3:2].ClC(OC(Cl)C)=O>ClC(Cl)C.CO>[CH:1]([O:4][C:5]1[CH:6]=[C:7]([C:11]23[CH2:30][CH:15]([CH2:16][CH:17]([N:19]4[C:20](=[O:29])[C:21]5[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=5)[C:27]4=[O:28])[CH2:18]2)[NH:14][CH2:13][CH:12]3[CH3:32])[CH:8]=[CH:9][CH:10]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 69194491HCID 69194491, compound

Product 1

HCID 69217200HCID 69217200, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 63651,1-DichloroethaneSolvent

Procedure

2-[5-(3-Isopropoxyphenyl)-2,4-dimethyl-2-aza-bicyclo[3 .3.1 ]non-7-yl]-isoindole-1,3-dione (2.5) (1.50 g, 3.5 mmol) was dissolved in dichloroethane and heated to reflux followed by the addition of 1-chloroethyl chloroformate (0.410 ml, 3.8 mmol). This solution was allowed to reflux for 3.5 hrs. The reaction was cooled and the solvent removed under reduced pressure. The crude material was taken up in ethyl acetate and washed with a saturated sodium bicarbonate solution (3×30 ml). The organic layer was collected, dried (Na2SO4) and the solvent removed under reduced pressure yielding crude product. This material was dissolved in methanol and refluxed overnight. The methanol was removed and the crude product dissolved in 1 N NaOH. The aqueous was extracted with 3:1 CH2Cl2:THF. The combined organic layers were collected, dried (Na2SO4) and the solvent removed under reduced pressure yielding crude product. This product was used with out further purification.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. temperatureto reflux for 3.5 hrs
  4. temperatureThe reaction was cooled
  5. customthe solvent removed under reduced pressure
  6. washwashed with a saturated sodium bicarbonate solution (3×30 ml)
  7. customThe organic layer was collected
  8. dry with materialdried (Na2SO4)
  9. customthe solvent removed under reduced pressure
  10. customyielding crude product
  11. temperaturerefluxed overnight
  12. customThe methanol was removed
  13. dissolutionthe crude product dissolved in 1 N NaOH
  14. extractionThe aqueous was extracted with 3:1 CH2Cl2
  15. customThe combined organic layers were collected
  16. dry with materialdried (Na2SO4)
  17. customthe solvent removed under reduced pressure
  18. customyielding crude product
  19. customThis product was used with out further purification

Sources & evidence

ORD record
ord-232a2f2184f6445d9174fb60f6f293a8
Source dataset
uspto-grants-2008_07
Patent number
US07399762B2

Reaction notes

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