Morpholine → HCID 19068966, compound

HRID 1735112Notes

Reaction equation

HRID 1735112 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[C:4]2[CH:14]=[C:15]([C:17]([OH:19])=O)[S:16][C:3]1=2.O=S(Cl)Cl.[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>C1COCC1>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[C:4]2[CH:14]=[C:15]([C:17]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[O:19])[S:16][C:3]1=2

Participants

5

Reactant 3

HCID 8083MorpholineHCID 24386Thionyl ChlorideHCID 19068968HCID 19068968, compound

Product 1

HCID 19068966HCID 19068966, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

280 mg of (68) was added to 25 ml of THF, 0.5 ml of SOCl2 was added, and the reaction left with stirring for 1 hour. 1 ml of morpholine was added in portions, and stirring continued. The precipitated morpholine hydrochloride was filtered off, and the solvent evaporated. The residue was purified by column chromatography on silica gel, using MeOH in CH2Cl2, 1+9 as the eluent. MeOH was added to the pooled fractions to precipitate the product, giving after filtration and drying 50 mg of (69). M.p. 250°-2° C.

Workup

  1. additionwas added
  2. waitthe reaction left
  3. stirringstirring
  4. filtrationThe precipitated morpholine hydrochloride was filtered off
  5. customthe solvent evaporated
  6. customThe residue was purified by column chromatography on silica gel
  7. additionMeOH was added to the pooled fractions
  8. customto precipitate the product
  9. customgiving
  10. filtrationafter filtration
  11. dry with materialdrying 50 mg of (69)

Sources & evidence

ORD record
ord-1cb8ecfd52f04cc589a2e06e5bcfde42
Source dataset
uspto-grants-1996_07
Patent number
US05536721

Reaction notes

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