Nitrogen → HCID 69671316, compound

HRID 714208Notes

Reaction equation

HRID 714208 reaction equation
N#N.Cl.[F:4][C:5]1([F:10])[CH2:9][CH2:8][NH:7][CH2:6]1.Cl[CH2:12][CH2:13][O:14][CH2:15][CH2:16][OH:17].C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1>[F:4][C:5]1([F:10])[CH2:9][CH2:8][N:7]([CH2:12][CH2:13][O:14][CH2:15][CH2:16][OH:17])[CH2:6]1

Participants

6

Reactant 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 123612-(Chloroethoxy)ethanolHCID 249034823,3-Difluoropyrrolidine hydrochloride

Product 1

HCID 69671316HCID 69671316, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a solution of 3,3-difluoropyrrolidine hydrochloride (258 mg, 1.74 mmol) and 2-(2-chloroethoxy)ethanol (3.77 mL, 34.83 mmol) in dry toluene (10 mL) were added K2CO3 (1.32 g, 9.58 mmol) and KI (29 mg, 0.17 mmol). The reaction mixture was stirred at reflux for 2 d. The mixture was cooled down to rt, filtered and concentrated under reduced pressure. The crude residue was purified by FC(CH2Cl2/MeOH/NH4OH, 1:0:0→98:2:0.5) and the title compound obtained as a pale yellow oil.

Workup

  1. temperatureat reflux for 2 d
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customThe crude residue was purified by FC(CH2Cl2/MeOH/NH4OH, 1:0:0→98:2:0.5)

Sources & evidence

ORD record
ord-90c636aca70c43c4a7453beefa23dbbb
Source dataset
uspto-grants-2015_11
Patent number
US09187435B2

Reaction notes

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