Iodoethane → HCID 67980529, compound

HRID 1400044Notes

Reaction equation

HRID 1400044 reaction equation
[C:1]1(N)C(F)=C(F)C(F)=C(N)[C:2]=1F.Cl.Cl.[N:15]1([C:21]2[CH:26]=[CH:25][C:24]([C@@:27]34[CH2:32][C@@H:31]3[CH2:30][NH:29][CH2:28]4)=[CH:23][CH:22]=2)[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.CCN(C(C)C)C(C)C.C(I)C>CN(C=O)C.O>[CH2:1]([N:29]1[CH2:30][C@@H:31]2[C@@:27]([C:24]3[CH:23]=[CH:22][C:21]([N:15]4[CH2:20][CH2:19][O:18][CH2:17][CH2:16]4)=[CH:26][CH:25]=3)([CH2:32]2)[CH2:28]1)[CH3:2]

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 81531DiisopropylethylamineHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 67980619HCID 67980619, compound

Product 1

HCID 67980529HCID 67980529, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of dihydrochloride salt of (1R,5S)-(4-morpholin-4-yl-phenyl)-3-aza-bicyclo[3.1.0]hexane (5.0 g, 17.8 mmol) in DMF (20 mL) were added DIPEA (12.7 mL, 71.3 mmol) and ethyl iodide (2.14 mL, 26.7 mmol) at r.t. and progress of the reaction was monitored by TLC. On completion, the reaction mixture was diluted with water (10 mL) and extracted with ethyl acetate (3×20 mL). The organic layer was washed with brine (2×10 mL), dried over anhydrous sodium sulphate and concentrated in vacuo. The residue was purified by column chromatography (silica gel, 0.2:9.8 MeOH:CHCl3) to provide the title compound as viscous liquid (2.3 g, 47%).

Workup

  1. extractionextracted with ethyl acetate (3×20 mL)
  2. washThe organic layer was washed with brine (2×10 mL)
  3. dry with materialdried over anhydrous sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (silica gel, 0.2:9.8 MeOH:CHCl3)

Sources & evidence

ORD record
ord-6217e6f1ffbe4fbbb01d35b8bf1716bd
Source dataset
uspto-grants-2014_12
Patent number
US08906913B2

Reaction notes

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