Morpholine → HCID 13013938, compound

HRID 444152Notes

Reaction equation

HRID 444152 reaction equation
Cl[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([C:13]([O:15][CH3:16])=[O:14])=[CH:12][C:7]=2[S:6](=[O:18])(=[O:17])[C:5]2[CH:19]=[CH:20][CH:21]=[CH:22][C:4]=2[N:3]=1.[NH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>C(#N)C>[O:26]1[CH2:27][CH2:28][N:23]([C:2]2[C:8]3[CH:9]=[CH:10][C:11]([C:13]([O:15][CH3:16])=[O:14])=[CH:12][C:7]=3[S:6](=[O:18])(=[O:17])[C:5]3[CH:19]=[CH:20][CH:21]=[CH:22][C:4]=3[N:3]=2)[CH2:24][CH2:25]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 13013934HCID 13013934, compound

Product 1

HCID 13013938HCID 13013938, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Reflux a mixture of 5.025 mg (15 mmole) of the 11-chloro ester of Example 14. 3.119 gm of morpholine and 75 ml of acetonitrile for 2 hours. Distill off the acetonitrile under a vacuum and dissolve the residue in 45 ml of methanol at room temperature. Filter, cool and separate the precipitate by filtration. Chromatograph over silica gel eluting with 1:4 ethylacetate in toluene. Recrystallize from ethanol to obtain the title product (m.p. 164°-166° C.).

Workup

  1. temperatureReflux
  2. distillationDistill off the acetonitrile under a vacuum
  3. dissolutiondissolve the residue in 45 ml of methanol at room temperature
  4. filtrationFilter
  5. temperaturecool
  6. customseparate the precipitate
  7. filtrationby filtration
  8. customRecrystallize from ethanol

Sources & evidence

ORD record
ord-a9c2c117ade44022800943b61dd76726
Source dataset
uspto-grants-1981_04
Patent number
US04263207

Reaction notes

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