1-Bromo-2-Chloroethane → 1-(2-Chloroethyl)-4,4-difluoropiperidine

HRID 2282234Notes

Reaction equation

HRID 2282234 reaction equation
[F:1][C:2]1([F:8])[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][CH2:17][Cl:18]>CC(C)=O>[Cl:18][CH2:17][CH2:16][N:5]1[CH2:6][CH2:7][C:2]([F:8])([F:1])[CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 27583524,4-Difluoropiperidine

Product 1

HCID 179639191-(2-Chloroethyl)-4,4-difluoropiperidineYield 16.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4,4-difluoropiperidine (1.00 g, 6.35 mmol) in acetone (15 mL), were added potassium carbonate (2.19 g, 15.9 mmol) and 1-bromo-2-chloroethane (635 μL, 7.62 mmol) and the mixture was stirred for 8 h at 50° C. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (EtOAc/hexane=0/100→30/70) to obtain title compound (188 mg, 16%) as a pale yellow oil.

Workup

  1. customInsoluble materials were removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (EtOAc/hexane=0/100→30/70)

Sources & evidence

ORD record
ord-8706000adda24acea25cb71ee9802190
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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