Morpholine → HCID 19068966, compound

HRID 1957216Notes

Reaction equation

HRID 1957216 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.Cl.N1CCOCC1>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

6

Reactant 4

HCID 8083MorpholineHCID 24386Thionyl ChlorideHCID 197884Morpholine, hydrochloride (1:1)HCID 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 filtrered 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. customthe solvent evaporated
  5. customThe residue was purified by column chromatography on silica gel
  6. additionMeOH was added to the pooled fractions
  7. customto precipitate the product
  8. customgiving
  9. filtrationafter filtration
  10. dry with materialdrying 50 mg of (69)

Sources & evidence

ORD record
ord-4041411e34354ac59a5c90c7a9aeedd6
Source dataset
uspto-grants-1998_07
Patent number
US05783575

Reaction notes

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