Hydrochloric Acid → HCID 131714828, compound

HRID 2231732Notes

Reaction equation

HRID 2231732 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:13][N:12]([CH:14]([CH3:28])[CH2:15][C:16]3[CH:27]=[CH:26][C:19]([O:20][CH2:21][C:22]([NH:24][CH3:25])=O)=[CH:18][CH:17]=3)[CH2:11][CH2:10][O:9]2)[CH:5]=[CH:6][CH:7]=1.CO.[ClH:31]>O1CCCC1>[OH2:9].[ClH:1].[ClH:31].[CH3:25][NH:24][CH2:22][CH2:21][O:20][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][CH:14]([N:12]2[CH2:11][CH2:10][O:9][CH:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[CH2:13]2)[CH3:28])=[CH:27][CH:26]=1.[CH3:25][NH:24][CH2:22][CH2:21][O:20][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][CH:14]([N:12]2[CH2:11][CH2:10][O:9][CH:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[CH2:13]2)[CH3:28])=[CH:27][CH:26]=1.[ClH:1].[ClH:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 13851160HCID 13851160, compound

Product 1

HCID 131714828HCID 131714828, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 4[2-(2-[3-chlorophenyl]morpholino)propyl]phenoxy-N-methylacetamide (3.6 g) in dry tetrahydrofuran (80 ml) was added borane-methyl sulphide complex (10 ml) in dry tetrahydrofuran (20 ml), under nitrogen. The solution was boiled under reflux for 4 hours, and, after cooling to room temperature, methanol (30 ml) was added carefully. This solution was allowed to stand overnight at room temperature, hydrogen chloride gas passed through for 10 mins, boiled under reflux for one hour, cooled and evaporated to dryness. Aqueous sodium carbonate was added to the residue and extracted with dichloromethane (x2). The combined organic extracts were washed with brine (x2), dried over magnesium sulphate, filtered and evaporated to dryness. Ethereal hydrogen chloride was added to the residue and the resultant solid recrystallised from methanol-ethyl acetate to give the title compound, m.p. 145°-55° C.

Workup

  1. temperatureunder reflux for 4 hours
  2. custompassed through for 10 mins
  3. temperatureunder reflux for one hour
  4. temperaturecooled
  5. customevaporated to dryness
  6. additionAqueous sodium carbonate was added to the residue
  7. extractionextracted with dichloromethane (x2)
  8. washThe combined organic extracts were washed with brine (x2)
  9. dry with materialdried over magnesium sulphate
  10. filtrationfiltered
  11. customevaporated to dryness
  12. additionEthereal hydrogen chloride was added to the residue
  13. customthe resultant solid recrystallised from methanol-ethyl acetate

Sources & evidence

ORD record
ord-65be81069d8247c593a4fc61315c75d6
Source dataset
uspto-grants-1988_11
Patent number
US04783460

Reaction notes

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