Hydrochloric Acid → HCID 10861106, compound

HRID 324621Notes

Reaction equation

HRID 324621 reaction equation
C([O:4][C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][C@H:11]2[CH2:14][CH2:15][NH:16][C:17](=[O:20])[CH2:18][CH3:19])=[CH:7][C:6]=1[Br:21])C=C.O.Cl.C(OCC)(=O)C.C(N(CC)[C:33]1[CH:38]=CC=C[CH:34]=1)C>>[CH2:38]([C:13]1[C:5]([OH:4])=[C:6]([Br:21])[CH:7]=[C:8]2[C:12]=1[C@H:11]([CH2:14][CH2:15][NH:16][C:17](=[O:20])[CH2:18][CH3:19])[CH2:10][CH2:9]2)[CH:33]=[CH2:34]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 7061N,N-DiethylanilineHCID 8857Ethyl AcetateHCID 10871865N-[2-[(1S)-5-Bromo-2,3-dihydro-6-(2-propen-1-yloxy)-1H-inden-1-yl]ethyl]propanamide

Product 1

HCID 10861106HCID 10861106, compoundYield 80%

Conditions

Temperature
202.5 °C

Procedure

A suspension of (S)-N-[2-(6-allyloxy-5-bromoindan-1-yl)ethyl]propionamide (50.75 g, 144 mmol.) in N,N-diethylaniline (150 mL) was stirred for 2.5 hours at 200-205° C. under argon atmosphere. The reaction mixture was cooled, followed by distilling off N,N-diethylaniline under reduced pressure to leave an oily residue. To the residue were added water (50 mL), 2N HCl (50 mL) and ethyl acetate (100 mL). The mixture was subjected to extraction twice to extract the organic matter. The extract solution was washed with a saturated aqueous saline solution and water, which was then dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was purified by means of silica gel column chromatography (ethyl acetate:hexane=7:3) to afford the title compound (yield 40.6 g, 80%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. distillationby distilling off N,N-diethylaniline under reduced pressure
  3. customto leave an oily residue
  4. extractionThe mixture was subjected to extraction twice
  5. extractionto extract the organic matter
  6. washThe extract solution was washed with a saturated aqueous saline solution and water, which
  7. dry with materialwas then dried over anhydrous magnesium sulfate
  8. distillationby distilling off the solvent under reduced pressure
  9. customThe residue was purified by means of silica gel column chromatography (ethyl acetate:hexane=7:3)

Sources & evidence

ORD record
ord-2205d887edf74611bc20eed20ca81ca5
Source dataset
uspto-grants-2001_04
Patent number
US06218429B1

Reaction notes

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