Ethyl Acrylate → HCID 22503716, compound

HRID 2186687Notes

Reaction equation

HRID 2186687 reaction equation
C([N:9]1[CH2:22][CH2:21][C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[NH:13][C:12]=2[CH2:11][CH2:10]1)(=O)C1C=CC=CC=1.[C:23](=[O:26])([O-:25])[O-].[Cs+].[Cs+].[C:29]([O:33]CC)(=[O:32])[CH:30]=[CH2:31]>C(#N)C.CN(C=O)C.O>[C:29]([OH:33])(=[O:32])[C:23]([OH:25])=[O:26].[CH:18]1[C:19]2[C:20]3[CH2:21][CH2:22][NH:9][CH2:10][CH2:11][C:12]=3[N:13]3[C:14]=2[C:15]([C:29](=[O:32])[CH2:30][CH2:31]3)=[CH:16][CH:17]=1

Participants

7

Reactant 3

HCID 8821Ethyl AcrylateHCID 10796Cesium carbonateHCID 22503722HCID 22503722, compound

Product 1

HCID 22503716HCID 22503716, compoundYield 166.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 3-benzoyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (5.00 g, 17.2 mmol), cesium carbonate (5.61 g, 17.2 mmol), and ethyl acrylate (1.90 mL, 17.5 mmol) in acetonitrile (250 mL) was heated under N2 at 50° C. for 5 h (reaction can also be run in DMF at room temperature). Cooled to room temperature, diluted with H2O, and extracted with EtOAc. The combined organic extracts were washed with saturated aqueous NaCl, dried over Na2SO4, decanted, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography with EtOAc/hexanes (2: 1) to give 4.82 g (72%) of the title compound as a yellow oil. 1H NMR (CDCl3) δ 7.57-7.38, 7.32, 7.23-7.07, 4.49-4.33, 4.20-4.02, 3.77-3.66, 3.28-3.13, 2.94, 2.72, 1.24; IR (liq.) 2981, 1731, 1631, 1467, 1445, 1422, 1381, 1368, 1349, 1319, 1295, 1272, 1242, 1187, 742, 707 cm−1; MS (ESI) 391.0 (M++H).

Workup

  1. customreaction
  2. temperatureCooled to room temperature
  3. extractionextracted with EtOAc
  4. washThe combined organic extracts were washed with saturated aqueous NaCl
  5. dry with materialdried over Na2SO4
  6. customdecanted
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by silica gel chromatography with EtOAc/hexanes (2: 1)

Sources & evidence

ORD record
ord-ae1bcd3d945340369e133ea8053672e0
Source dataset
uspto-grants-2002_06
Patent number
US06407092B1

Reaction notes

Loading…