1,2-Dichloroethane → 2-(4,4-Difluoropiperidin-1-yl)acetyl chloride

HRID 1094715Notes

Reaction equation

HRID 1094715 reaction equation
Cl.[F:2][C:3]1([F:9])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.Cl[CH2:11][C:12]([OH:14])=O.C(Cl)C[Cl:17]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[F:2][C:3]1([F:9])[CH2:8][CH2:7][N:6]([CH2:11][C:12]([Cl:17])=[O:14])[CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 300Chloroacetic AcidHCID 27583514,4-Difluoropiperidine hydrochloride

Product 1

HCID 598428832-(4,4-Difluoropiperidin-1-yl)acetyl chlorideYield 88%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4,4-difluoropiperidine hydrochloride (1.44 g, 9 mmol) in DCM (15 mL) was added chloroacetic acid (0.94 g, 10 mmol), TEA (1.5 mL), EDC (3.82 g, 20 mmol) and DMAP (cat.). The reaction mixture was stirred at RT overnight. The contents were transferred to a separatory funnel and DCM layer was washed saturated NaHCO3 solution, dried over anhydrous Na2SO4. The crude product was purified by flash column chromatography using 3:1 Pet. Ether:DCM in. 2-(4,4-difluoropiperidin-1-yl)acetyl chloride was isolated as a white solid weighing 1.57 g (yield: 88%).

Workup

  1. customThe contents were transferred to a separatory funnel
  2. washDCM layer was washed saturated NaHCO3 solution
  3. dry with materialdried over anhydrous Na2SO4
  4. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-e773384fbbc44ca39257eae04f47bb2d
Source dataset
uspto-grants-2012_03
Patent number
US08133998B2

Reaction notes

Loading…