Potassium Iodide → 8-(5,6-dichloro-1H-benzimidazol-2-yl)-4-(2-morpholine-4-yl-ethyl)-3,4-dihydro-2H-benzo[1,4]oxazine

HRID 1809128Notes

Reaction equation

HRID 1809128 reaction equation
[Cl:1][C:2]1[C:20]([Cl:21])=[CH:19][C:5]2[NH:6][C:7]([C:9]3[C:14]4[O:15][CH2:16][CH2:17][NH:18][C:13]=4[CH:12]=[CH:11][CH:10]=3)=[N:8][C:4]=2[CH:3]=1.Cl[CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.[I-].[K+].C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[C:20]([Cl:21])=[CH:19][C:5]2[NH:6][C:7]([C:9]3[C:14]4[O:15][CH2:16][CH2:17][N:18]([CH2:23][CH2:24][N:25]5[CH2:30][CH2:29][O:28][CH2:27][CH2:26]5)[C:13]=4[CH:12]=[CH:11][CH:10]=3)=[N:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 767274-(2-Chloroethyl)morpholineHCID 670948938-(5,6-dichloro-1H-benzo[d]imidazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine2×

Product 1

HCID 670949588-(5,6-dichloro-1H-benzimidazol-2-yl)-4-(2-morpholine-4-yl-ethyl)-3,4-dihydro-2H-benzo[1,4]oxazineYield 92.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.5 g (14 mmol) of 8-(5,6-dichloro-1H-benzo[d]imidazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine (compound 1a) obtained in Example 5 was dissolved in 100 mL of dimethylformamide. 1.3 g (7 mmol) of 4-(2-chloroethyl)morpholine, 0.58 g (3.5 mmol) of potassium iodide and 0.97 g (7 mmol) of K2CO3 were added thereto, followed by irradiation of microwave at 110° C. for 10 min. The reaction mixture was concentrated under reduced pressure, followed by dilution with ethyl acetate. The resulting product was washed with distilled water and saturated sodium chloride solution, followed by drying over magnesium sulfate and concentrating under reduced pressure. The resulting residue was subjected to column chromatography (ethyl acetate/hexane=1/1) to obtain the title compound (2.8 g, yield: 91%).

Workup

  1. customfollowed by irradiation of microwave at 110° C. for 10 min
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. washThe resulting product was washed with distilled water and saturated sodium chloride solution
  4. dry with materialby drying over magnesium sulfate
  5. concentrationconcentrating under reduced pressure

Sources & evidence

ORD record
ord-1d8e9a4c9c124238a505ae1c33f441b5
Source dataset
uspto-grants-2013_01
Patent number
US08362012B2

Reaction notes

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