1-Chloroethyl chloroformate → HCID 17952146, compound

HRID 456557Notes

Reaction equation

HRID 456557 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:22]3[C:17](=[CH:18][C:19]([C:23]([F:26])([F:25])[F:24])=[CH:20][CH:21]=3)[N:16]([CH3:27])[N:15]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.[Cl:28]C(OC(Cl)C)=O>C(Cl)Cl>[ClH:28].[CH3:27][N:16]1[C:17]2[C:22](=[CH:21][CH:20]=[C:19]([C:23]([F:24])([F:26])[F:25])[CH:18]=2)[C:14]([CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[N:15]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 18436984HCID 18436984, compound

Product 1

HCID 17952146HCID 17952146, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the 3-(1-benzyl-piperidin-4-yl)-1-methyl-6-trifluoromethyl-1H-indazole (1.41 g, 3.78 mmol) in DCM (20 mL) was added 1-chloroethyl chloroformate (0.49 mL, 4.50 mmol). The resulting solution was stirred at room temperature overnight when the volitiles were removed in vacuo. The residue was taken un in methanol (20 mL) and the resulting solution was heated at reflux for 1 hour. The mixture was cooled to room temperature and the solution was evaporated. The residue was taken up in EtOAc and the solid product was collected by filtration yielding 1.03 g (86%) of the HCl salt as a white solid.

Workup

  1. customwere removed in vacuo
  2. temperaturethe resulting solution was heated
  3. temperatureat reflux for 1 hour
  4. temperatureThe mixture was cooled to room temperature
  5. customthe solution was evaporated
  6. filtrationthe solid product was collected by filtration

Sources & evidence

ORD record
ord-b13b1c916e07486f8d76182ddaba5972
Source dataset
uspto-grants-2007_03
Patent number
US07186724B2

Reaction notes

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