1-Chloroethyl chloroformate → HCID 131715638, compound

HRID 845670Notes

Reaction equation

HRID 845670 reaction equation
F[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7](C1C=CC(C(F)(F)F)=CC=1)[N:6]=[C:5]2C1CCN(C)CC1.[Cl:28][CH:29](OC(Cl)=O)[CH3:30]>ClCCCl>[ClH:28].[N:6]1([C:3]2[CH:2]=[CH:10][CH:9]=[C:8]3[C:4]=2[CH:5]=[N:6][NH:7]3)[CH2:30][CH2:29][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 14032594HCID 14032594, compound

Product 1

HCID 131715638HCID 131715638, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 5-fluoro-1-[4-(trifluoromethyl)phenyl]-3-(1-methyl-4-piperidinyl)-1H-indazole (13.2 g, 0.035 moles) in 1,2-dichloroethane (35 ml) at 0° C. was added 1-chloroethylchloroformate (3.9 ml, 0.035 moles). The reaction was stirred for 15 minutes at 0° and then for 4 hours at ambient temperature. The solvent was removed and then methanol (90 ml) was added. The mixture was refluxed for 1 hour and then the methanol was removed which left 17.8 g of a solid. The product was recrystallized twice from isopropyl alcohol to yield 6.3 g (45%) of 5-fluoro-1-[4-(trifluoromethyl)phenyl]-3-(4-piperidinyl-1H-indazole hydrochloride, mp 276°-278°.

Workup

  1. waitfor 4 hours at ambient temperature
  2. customThe solvent was removed
  3. additionmethanol (90 ml) was added
  4. temperatureThe mixture was refluxed for 1 hour
  5. customthe methanol was removed which
  6. waitleft 17.8 g of a solid
  7. customThe product was recrystallized twice from isopropyl alcohol

Sources & evidence

ORD record
ord-028bc113eb0848fa83c9c27915c363fc
Source dataset
uspto-grants-1988_07
Patent number
US04758668

Reaction notes

Loading…