1-Chloroethyl chloroformate → HCID 17952146, compound

HRID 2111744Notes

Reaction equation

HRID 2111744 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 volatiles 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-2277ed719b3042b9becd40c4230fd72c
Source dataset
uspto-grants-2009_04
Patent number
US07521445B2

Reaction notes

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