Potassium Carbonate → ethyl 7-(dibenzo[b,f][1,4]oxazepin-10(11H)-yl)heptanoate

HRID 718091Notes

Reaction equation

HRID 718091 reaction equation
[CH:1]1[C:6]2[CH2:7][NH:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[O:11][C:5]=2[CH:4]=[CH:3][CH:2]=1.I[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(OCC)(=O)C>[CH:1]1[C:6]2[CH2:7][N:8]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[O:11][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 64893310,11-Dihydrodibenzo(b,f)(1,4)oxazepineHCID 10660673Ethyl 7-iodoheptanoate

Product 1

HCID 59783580ethyl 7-(dibenzo[b,f][1,4]oxazepin-10(11H)-yl)heptanoateYield 37%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

Title compound 398 (0.304 g, 1.54 mmol) was dissolved in acetonitrile (5.0 mL) and the ethyl 7-iodoheptanoate (0.613 g, 2.16 mmol) and the potassium carbonate (0.639 g, 4.62 mmol) were added. The reaction mixture was stirred at 70° C. for 60 hours. The mixture was cooled down and diluted with ethyl acetate. The organic phase was washed with water and brine, dried over sodium sulfate, filtered and evaporated. The residue was purified by flash chromatography with 10% ethyl acetate in hexanes to afford title compound 399 (201 mg, 37%). MS (m/z): 354.2 (M+H).

Workup

  1. temperatureThe mixture was cooled down
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography with 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-4b64f278adb741249b3fd86d9f24e118
Source dataset
uspto-grants-2015_11
Patent number
US09193749B2

Reaction notes

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