1-Chloroethyl chloroformate → HCID 14032601, compound

HRID 1722178Notes

Reaction equation

HRID 1722178 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1)[N:6]=[C:5]2[CH:21]1[CH2:26][CH2:25][N:24](C)[CH2:23][CH2:22]1.[Cl:28]C(OC(Cl)=O)C>ClCCCl>[ClH:28].[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[CH:12]=[CH:13][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:15][CH:16]=1)[N:6]=[C:5]2[CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 14032594HCID 14032594, compound

Product 1

HCID 14032601HCID 14032601, compoundYield 45%

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-6faa621d0abb40c4bfa03931dd706c7d
Source dataset
uspto-grants-1989_08
Patent number
US04853470

Reaction notes

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