3-(Benzhydrylidene-amino)-3-pyridin-4-ylmethyl-dihydro-furan-2-one → 3-Amino-3-pyridin-4-ylmethyl-dihydro-furan-2-one

HRID 1421911Notes

Reaction equation

HRID 1421911 reaction equation
C(=[N:14][C:15]1([CH2:21][C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)[CH2:19][CH2:18][O:17][C:16]1=[O:20])(C1C=CC=CC=1)C1C=CC=CC=1>Cl.C1COCC1>[NH2:14][C:15]1([CH2:21][C:22]2[CH:23]=[CH:24][N:25]=[CH:26][CH:27]=2)[CH2:19][CH2:18][O:17][C:16]1=[O:20]

Participants

4

Reactant 1

HCID 541390243-(Benzhydrylidene-amino)-3-pyridin-4-ylmethyl-dihydro-furan-2-one

Product 1

HCID 540640063-Amino-3-pyridin-4-ylmethyl-dihydro-furan-2-oneYield 69.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-(Benzhydrylidene-amino)-3-pyridin-4-ylmethyl-dihydro-furan-2-one (1.67 g, 4.69 mMol) was dissolved in a solution of 1 N HCl (20 mL) in THF (50 mL). The mixture was stirred for 1 hour at ambient temperature after which time it was partitioned between ethyl ether (Et2O) and water. The water layer was washed again with Et2O and then adjusted to pH 8 with NaHCO3. The aqueous layer was then extracted with CH2Cl2. The CH2Cl2 layer was dried over Na2SO4, filtered and concentrated under vacuum to give 630 mg of the titled compound as an oil.

Workup

  1. customwas partitioned between ethyl ether (Et2O) and water
  2. washThe water layer was washed again with Et2O
  3. extractionThe aqueous layer was then extracted with CH2Cl2
  4. dry with materialThe CH2Cl2 layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9eda1b6257da4b90a90664fab833796f
Source dataset
uspto-grants-2000_06
Patent number
US06080769

Reaction notes

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