Diisopropylethylamine → HCID 71182928, compound

HRID 1891396Notes

Reaction equation

HRID 1891396 reaction equation
Cl.[OH:2][CH:3]1[CH2:10][CH:6]2[CH2:7][NH:8][CH2:9][CH:5]2[CH2:4]1.F[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=1[F:21].C(N(CC)C(C)C)(C)C>C(#N)C>[F:21][C:13]1[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=[CH:17][C:12]=1[N:8]1[CH2:9][CH:5]2[CH2:4][CH:3]([OH:2])[CH2:10][CH:6]2[CH2:7]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 77259051OCTAHYDROCYCLOPENTA[C]PYRROL-5-OL HCL

Product 1

HCID 71182928HCID 71182928, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The octahydro-5-hydroxycyclopenta[c]pyrrol hydrochloride (44.4 mmol) prepared in the step 1 was dissolved in 100 ml of acetonitrile, and 4.91 ml (44.4 mmol) of 1,2-difluoro-4-nitrobenzene and 23.20 ml (133.2 mmol) of N,N-diisopropylethylamine were added, and the mixture was heat to reflux for 6 hours. After the reaction was completed, the temperature was lowered to room temperature, and the mixture was concentrated under reduced pressure to remove the solvent. The solvent-free concentrate was dissolved in ethyl acetate, and washed with distilled water, and then, the organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure to obtain the title compound, of which NMR data is as follow.

Workup

  1. temperaturethe mixture was heat
  2. temperatureto reflux for 6 hours
  3. customwas lowered to room temperature
  4. concentrationthe mixture was concentrated under reduced pressure
  5. customto remove the solvent
  6. concentrationThe solvent-free concentrate
  7. dissolutionwas dissolved in ethyl acetate
  8. washwashed with distilled water
  9. dry with materialthe organic layer was dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ade7932ce9fd49199bdee69438c3cd31
Source dataset
uspto-grants-2013_08
Patent number
US08507540B2

Reaction notes

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