Iodoethane → HCID 46219101, compound

HRID 575945Notes

Reaction equation

HRID 575945 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1([O:14][CH3:15])[CH2:13][CH2:12][NH:11][CH2:10]1.[C:16](#N)[CH3:17].C(=O)([O-])[O-].[Na+].[Na+].ICC>O>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1([O:14][CH3:15])[CH2:13][CH2:12][N:11]([CH2:16][CH3:17])[CH2:10]1

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 46219100HCID 46219100, compound

Product 1

HCID 46219101HCID 46219101, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 3-(2,3-difluorophenyl)-3-methoxypyrrolidine (0.4 g, 1.87 mmol), acetonitrile (5 ml), sodium carbonate (0.52 g, 3.74 mmol) and iodoethane (0.28 g, 1.87 mmol) was heated at 110° C. in a sealed tube under microwave irradiation for 10 minutes. Water (30 ml) was added and the aqueous phase was extracted with ethyl acetate (2×50 ml), the combined organic phases was dried (MgsO4) and evaporated to give the crude product (0.45 g). Purification by flash chromatography (ethyl acetate/methanol 1:1) and by HPLC on waters OBD C18, 5 μm (MeOH/33 mM NH3, 20:80 to 50:50) gave the title compound (0.12 g, 27%). The amine was converted to the fumaric acid salt and recrystallized from methanol/diethyl ether/diisopropyl ether: M.p. 94-98° C. MS m/z (rel. intensity, 70 eV) 241 (M+, 5), 226 (54), 211 (27), 141 (50), 71 (bp).

Workup

  1. extractionthe aqueous phase was extracted with ethyl acetate (2×50 ml)
  2. customthe combined organic phases was dried (MgsO4)
  3. customevaporated
  4. customto give the crude product (0.45 g)
  5. customPurification by flash chromatography (ethyl acetate/methanol 1:1)

Sources & evidence

ORD record
ord-2bfa6d051381407f98f092a53eb0725f
Source dataset
uspto-grants-2015_05
Patent number
US09035073B2

Reaction notes

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