Hydrochloric Acid → HCID 10861106, compound

HRID 1636594Notes

Reaction equation

HRID 1636594 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-5fcc2ba1537b4dffa5ae4850320b49ce
Source dataset
uspto-grants-2000_03
Patent number
US06034239

Reaction notes

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