1-Chloroethyl chloroformate → HCID 45099758, compound

HRID 1350434Notes

Reaction equation

HRID 1350434 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:27]=[CH:26][O:25][CH:24]=1)C1C=CC=CC=1.C(N1CCN(CC2C=CC=CC=2)C[C@@H]1CC)C1C=CC=CC=1.ClC(OC(Cl)C)=O>ClCCCl.CO>[O:25]1[CH:26]=[CH:27][C:23]([CH2:22][CH2:21][C@H:9]2[CH2:10][NH:11][CH2:12][CH2:13][NH:8]2)=[CH:24]1

Participants

6

Reactant 3

HCID 5213051-Chloroethyl chloroformateHCID 21093633HCID 21093633, compoundHCID 58860637HCID 58860637, compound

Product 1

HCID 45099758HCID 45099758, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolvent

Conditions

Temperature
83 °C

Procedure

Dissolve a mixture of (S)-1,4-dibenzyl-2-(2-furan-3-yl-ethyl)-piperazine and (S)-1,4-dibenzyl-2-ethyl-piperazine (2.29 g, 6.35 mmol) in 1,2-dichloroethane (10 mL). Cool on an ice bath and add 1-chloroethyl chloroformate (2.06 ml, 19.1 mmol) dropwise. Remove ice bath and heat to 83° C. for 5.5 h. Concentrate the reaction, dissolve the residue in methanol (50 mL) and heat to reflux for 2 h. Cool to ambient temperature and stir 18 h. Filter and concentrate to a solid. Purify by silica gel chromatography using 7N ammonia in methanol-methylene chloride (2.5%–10%) as the eluent to give 330 mg (29%) of the title compound: mp 112–4° C. Mass spectrum (ion spray): m/z=181 (M+1).

Workup

  1. dissolutionDissolve
  2. temperatureCool on an ice bath
  3. concentrationConcentrate
  4. customthe reaction
  5. temperatureheat
  6. temperatureto reflux for 2 h
  7. temperatureCool to ambient temperature
  8. filtrationFilter
  9. concentrationconcentrate to a solid
  10. customPurify by silica gel chromatography

Sources & evidence

ORD record
ord-833829287eed4ef3a14eb07066853334
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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