Morpholine → HCID 86734091, compound

HRID 1288183Notes

Reaction equation

HRID 1288183 reaction equation
[CH3:1][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:5]=[C:4]2[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][C:19](O)=[O:20])[CH2:15][CH2:16][C:3]=12.[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.S(Cl)([Cl:30])=O>>[ClH:30].[ClH:30].[CH3:1][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:5]=[C:4]2[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][C:19]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[O:20])[CH2:15][CH2:16][C:3]=12

Participants

4

Reactant 3

HCID 8083MorpholineHCID 24386Thionyl ChlorideHCID 21503395HCID 21503395, compound

Product 1

HCID 86734091HCID 86734091, compound

Procedure

3.3 gm (9.25 millimols) of 3-[1,2,4,5-tetrahydro-11-methyl-3H-azepino[4,5-b] quinoline-3yl]propionic acid were converted into the acid chloride with 50 ml of thionylchloride. After distilling off the excess thionyl chloride, the residue was dissolved in 100 ml of benzene, and the solution was heated at its boiling point with 3 ml (35 millimols) of morpholine for 3 hours. After filtering, the solvent was distilled off in vacuo. The residue was dissolved in 2 N sodium hydroxide, the solution was extracted with chloroform, and the chloroform phase was dried over sodium sulfate and evaporated. The evaporation residue was dissolved in hot isopropanol and acidified with isopropanolic hydrochloric acid. Upon cooling, the dihydrochloride crystallized out.

Workup

  1. distillationAfter distilling off the excess thionyl chloride
  2. dissolutionthe residue was dissolved in 100 ml of benzene
  3. temperaturethe solution was heated at its
  4. customfor 3 hours
  5. filtrationAfter filtering
  6. distillationthe solvent was distilled off in vacuo
  7. dissolutionThe residue was dissolved in 2 N sodium hydroxide
  8. extractionthe solution was extracted with chloroform
  9. dry with materialthe chloroform phase was dried over sodium sulfate
  10. customevaporated
  11. dissolutionThe evaporation residue was dissolved in hot isopropanol
  12. temperatureUpon cooling
  13. customthe dihydrochloride crystallized out

Sources & evidence

ORD record
ord-ae58a2e077d34b9198b3f064ce91f8cb
Source dataset
uspto-grants-1976_10
Patent number
US03987047

Reaction notes

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