Morpholine → HCID 12050572, compound

HRID 1634035Notes

Reaction equation

HRID 1634035 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:9](=[O:10])[CH2:8][S:7][CH:6]1[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=1.[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.C(N(CC)C(C)C)(C)C.CCOC(C)=O>CN(C=O)C>[F:17][C:13]1[CH:12]=[C:11]([CH:6]2[N:5]([CH2:4][CH2:3][CH2:2][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[C:9](=[O:10])[CH2:8][S:7]2)[CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 12050571HCID 12050571, compound

Product 1

HCID 12050572HCID 12050572, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

3-(3-Chloropropyl)-2-(3-fluorophenyl)-thiazolidin-4-one (1.15 mm, 0.315 g) and morpholine (1.15 mm, 0.1 g) are mixed in 20 mL DMF in the presence of N,N-diisopropylethylamine (1.15 mm, 0.2 mL) and a catalytic amount of KI. The mixture is heated at 60° C. for 24 hours, then 20 mL of EtOAc is added to the mixture. The organic layer is washed with brine and dried. The solvent is evaporated, and the residue is triturated with hexane, 0.31 g of the product is isolated (84%).

Workup

  1. washThe organic layer is washed with brine
  2. customdried
  3. customThe solvent is evaporated
  4. customthe residue is triturated with hexane

Sources & evidence

ORD record
ord-76bb82a2f0324c3a90dc5a0f813a9d0d
Source dataset
uspto-grants-2003_01
Patent number
US06506751B1

Reaction notes

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