1-Chloroethyl chloroformate → HCID 58860729, compound

HRID 1350408Notes

Reaction equation

HRID 1350408 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11](CC2C=CC=CC=2)[CH2:10][C@@H:9]1[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=1)C1C=CC=CC=1.ClC(OC(Cl)C)=O>ClC(Cl)C>[Cl:29][C:25]1[CH:24]=[C:23]([CH2:22][CH2:21][C@H:9]2[CH2:10][NH:11][CH2:12][CH2:13][NH:8]2)[CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 58860645HCID 58860645, compound

Product 1

HCID 58860729HCID 58860729, compoundYield 16.4%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Dissolve (S)-1,4-dibenzyl-2-[2-(3-chloro-phenyl)-ethyl]-piperazine (4.48 g, 11.07 mmol) in dichloroethane (40 ml). Cool the solution to 0° and then add 1-chloroethyl chloroformate (4.75 g, 33.21 mmol) dropwise. Warm the solution to ambient temperature and then heat it at reflux for 42 hours. Remove the dichloroethane under vacuum and reflux the resulting residue in methanol (100 ml) for 1 hour. Remove the methanol under vacuum and dissolve the resulting precipitate in 1N NaOH. Extract the aqueous layer with dichloromethane and then combine, wash (brine), dry (sodium sulfate), and reduce the extracts to residue. Purify the residue on silica gel using dichloromethane/2N ammonia in methanol (90:10) to give 407.6 mg (16%) of the title compound: mp 93°–97°; mass spectrum (ion spray): m/z=225.3 (M+1).

Workup

  1. temperatureCool the solution to 0°
  2. temperatureheat it
  3. temperatureat reflux for 42 hours
  4. customRemove the dichloroethane under vacuum
  5. temperaturereflux the resulting residue in methanol (100 ml) for 1 hour
  6. customRemove the methanol under vacuum
  7. dissolutiondissolve the resulting precipitate in 1N NaOH
  8. extractionExtract the aqueous layer with dichloromethane
  9. washwash (brine)
  10. dry with materialdry (sodium sulfate)
  11. customPurify the residue on silica gel

Sources & evidence

ORD record
ord-1a315d6524304c288652a5c9e096f7f0
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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