1-Chloroethyl chloroformate → HCID 58860692, compound

HRID 1350407Notes

Reaction equation

HRID 1350407 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][C:26]([Cl:29])=[CH:25][CH:24]=1)C1C=CC=CC=1.ClC(OC(Cl)C)=O>ClC(Cl)C>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:22][CH2:21][C@H:9]2[CH2:10][NH:11][CH2:12][CH2:13][NH:8]2)=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 58860671HCID 58860671, compound

Product 1

HCID 58860692HCID 58860692, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Dissolve (S)-1,4-dibenzyl-2-[2-(4-chloro-phenyl)-ethyl]-piperazine (4.74 g, 11.71 mmol) in dichloroethane (80 ml). Cool the solution to 0° and then add 1-chloroethyl chloroformate (7.95 g, 55.61 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 459.0 mg (18%) of the title compound: mp 140°–144°; 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-c9a00cba04af4f23a76fce3b387e9a4b
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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