HCID 86723341, compound → HCID 86723340, compound

HRID 1472493Notes

Reaction equation

HRID 1472493 reaction equation
Cl.[C:2]1([CH:8]([N:10]2[CH2:14][CH:13]([CH2:15][NH:16][CH:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH3:18])[O:12][C:11]2=[O:25])[CH3:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>ClCCl>[C:2]1([CH:8]([N:10]2[CH2:14][CH:13]([CH2:15][NH:16][CH:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH3:18])[O:12][C:11]2=[O:25])[CH3:9])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 86723341HCID 86723341, compound

Product 1

HCID 86723340HCID 86723340, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a reaction flask were added 6.10 g (20.49 mmol) of 1,3-bis-[1-phenylethylamino]-2-propanol (2a) and 60 ml of toluene. The mixture was cooled to 0° C. in an ice bath before 6.11 g (37.70 mmol) of carbonyldiimidazole was added and allowed to react for 30 minutes at 0° C. After the reaction was completed, the reaction mixture was washed with 5% aqueous HCl to separate an organic layer. The organic layer was then dried by anhydrous sodium sulfate and filtered, subsequently evaporated under reduced pressure for solvent removal. The residue obtained was subjected to recrystallization using acetone. White needle-shaped crystals of 3-(1-phenylethyl)-5-[(1-phenylethyl)aminomethyl]-1,3-oxazolidin-2-one hydrochloride (racemic hydrochloride of Ia) with a melting point >220° C. were obtained, and at a yield of 89%. The hydrochloride obtained was dissolved in an appropriate amount of dichloromethane and the resulting solution was washed with 10% aqueous NaOH solution to attain an alkaline pH. The resulting organic layer was then dried by anhydrous sodium sulfate and filtered, and subsequently evaporated under reduced pressure for solvent removal to give 3-(1-phenylethyl)-5-[(1-phenylethyl)aminomethyl]-1,3-oxazolidin-2-one (Ia) at a yield of 97%. HR-TOF-MS (+Q) m/z: 325.1912 (Calculated [C20H24N2O2+H]+: 325.1916).

Workup

  1. washthe resulting solution was washed with 10% aqueous NaOH solution
  2. dry with materialThe resulting organic layer was then dried by anhydrous sodium sulfate
  3. filtrationfiltered
  4. customsubsequently evaporated under reduced pressure for solvent removal

Sources & evidence

ORD record
ord-7f1cfff8b55d45e6bd78d410f0633cd2
Source dataset
uspto-grants-2015_04
Patent number
US09012631B2

Reaction notes

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