1-Chloroethyl chloroformate → HCID 68467381, compound

HRID 503009Notes

Reaction equation

HRID 503009 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2([C:19]3[N:23]([CH3:24])[C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[Cl:31])=[N:21][N:20]=3)[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C(Cl)(=O)OC(Cl)C>C(Cl)Cl>[Cl:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[C:22]1[N:23]([CH3:24])[C:19]([C:14]2([CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[CH2:15][CH2:16][CH2:17][CH2:18]2)=[N:20][N:21]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 68469653HCID 68469653, compound

Product 1

HCID 68467381HCID 68467381, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Benzyl-4-{1-[5-(2-chlorophenyl)-4-methyl-1,2,4-triazol-3-yl]cyclopentyl}piperidine (0.87 g) and 1-chloroethyl chlorocarbonate (0.24 ml) were reacted in methylene chloride (20 ml) at room temperature for 2.5 hours. The residue obtained by subjecting the reaction solution to evaporation under reduced pressure was heated and refluxed in methanol (20 ml). After concentration, dil. hydrochloric acid (30 ml) was added thereto and the whole washed with diethyl ether. After neutralization, the product was extracted with chloroform (20 ml×2) and the concentration residue was purified by silica gel column chromatography (methanol:chloroform=4:96) to obtain 4-{1-[5-(2-chlorophenyl)-4-methyl-1,2,4-triazol-3-yl]cyclopentyl}piperidine (0.553 g).

Workup

  1. customThe residue obtained
  2. customto evaporation under reduced pressure
  3. temperaturewas heated
  4. temperaturerefluxed in methanol (20 ml)
  5. concentrationAfter concentration, dil. hydrochloric acid (30 ml)
  6. additionwas added
  7. washthe whole washed with diethyl ether
  8. extractionAfter neutralization, the product was extracted with chloroform (20 ml×2)
  9. customthe concentration residue was purified by silica gel column chromatography (methanol:chloroform=4:96)

Sources & evidence

ORD record
ord-cda55d462a5e4628a22f08a13d7434d5
Source dataset
uspto-grants-2010_08
Patent number
US07776897B2

Reaction notes

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