1-Chloroethyl chloroformate → 4,4-Difluoropiperidine hydrochloride

HRID 1437279Notes

Reaction equation

HRID 1437279 reaction equation
[Cl:1]C(OC(Cl)C)=O.C([N:15]1[CH2:20][CH2:19][C:18]([F:22])([F:21])[CH2:17][CH2:16]1)C1C=CC=CC=1>C(Cl)Cl>[ClH:1].[F:21][C:18]1([F:22])[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 27828111-benzyl-4,4-difluoropiperidine

Product 1

HCID 27583514,4-Difluoropiperidine hydrochlorideYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In an argon atmosphere, 1-chloroethyl chloroformate (2.62 mL) was added dropwise to the above-obtained N-benzyl-4,4-difluoropiperidine (4.66 g) in methylene chloride (93 mL) at 0° C., and the resultant mixture was stirred at 55° C. for 2 hours, and then cooled in air. The reaction solvent was removed under reduced pressure, and the residue in methanol (93 mL) was refluxed under heat for 4 hours, and then cooled in air. The reaction solvent was removed under reduced pressure, to thereby give the title compound as a solid (3.03 g, 87%).

Workup

  1. temperaturecooled in air
  2. customThe reaction solvent was removed under reduced pressure
  3. temperaturethe residue in methanol (93 mL) was refluxed
  4. temperatureunder heat for 4 hours
  5. temperaturecooled in air
  6. customThe reaction solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-cc5da8b7849f47a09569b63285e0781c
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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