1-Chloroethyl chloroformate → HCID 58860679, compound

HRID 1350406Notes

Reaction equation

HRID 1350406 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]=[CH:25][C:24]=1[Cl:29])C1C=CC=CC=1.ClC(OC(Cl)C)=O>ClC(Cl)C>[Cl:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[CH2:22][CH2:21][C@H:9]1[CH2:10][NH:11][CH2:12][CH2:13][NH:8]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 58860737HCID 58860737, compound

Product 1

HCID 58860679HCID 58860679, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Dissolve (S)-1,4-dibenzyl-2-[2-(2-chloro-phenyl)-ethyl]-piperazine (2.59 g, 6.38 mmol) in dichloroethane (30 ml). Cool the solution to 0° and then add 1-chloroethyl chloroformate (2.74 g, 19.15 mmol) dropwise. Warm the solution to ambient temperature and then heat it at reflux for 15 hours. Remove the dichloroethane under vacuum and reflux the resulting residue in methanol 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 482.4 mg (34%) of the title compound: mass spectrum (ion spray): m/z=225.3 (M+1).

Workup

  1. temperatureCool the solution to 0°
  2. temperatureheat it
  3. temperatureat reflux for 15 hours
  4. customRemove the dichloroethane under vacuum
  5. temperaturereflux the resulting residue in methanol 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-56d8684348564cf285e88a11eb59c34c
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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