Water → HCID 20225053, compound

HRID 1249169Notes

Reaction equation

HRID 1249169 reaction equation
[ClH:1].[Cl:2][C:3]1[CH:4]=[C:5]([C:10]2([CH2:14][NH:15][C:16](=O)[CH2:17][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[CH2:13][CH2:12][CH2:11]2)[CH:6]=[CH:7][C:8]=1[Cl:9].O>O1CCCC1>[OH2:21].[ClH:2].[ClH:1].[O:21]1[CH2:20][CH2:19][N:18]([CH2:17][CH2:16][NH:15][CH2:14][C:10]2([C:5]3[CH:6]=[CH:7][C:8]([Cl:9])=[C:3]([Cl:2])[CH:4]=3)[CH2:11][CH2:12][CH2:13]2)[CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 962WaterHCID 20225044HCID 20225044, compound

Product 1

HCID 20225053HCID 20225053, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-methyl sulphide complex (2 ml) was added to a refluxing solution of the morpholinoacetamide prepared in a similar manner to that described above in the form of its free base (3.6 g) in dry tetrahydrofuran (20 ml) and the mixture heated under reflux for four hours. The mixture was cooled and water (10 ml) added. Dimethylsulphide and tetrahydrofuran were removed by evaporation and excess 5N hydrochloric acid added. The solution was basified and extracted with ether. Hydrogen chloride gas was passed into the washed and dried ether extract. Evaporation to dryness gave a residue which was triturated with dry ether and recrystallised from an 8:2 mixture of propan-2-ol and ethanol to give N-(2-morpholinoethyl)-[1-(3,4-dichlorophenyl)cyclobutyl]methylamine dihydrochloride monohydrate (m.p. 230°-244° C.).

Workup

  1. customprepared in a similar manner to that
  2. temperaturethe mixture heated
  3. temperatureunder reflux for four hours
  4. temperatureThe mixture was cooled
  5. customDimethylsulphide and tetrahydrofuran were removed by evaporation and excess 5N hydrochloric acid
  6. additionadded
  7. extractionextracted with ether
  8. washwashed
  9. extractiondried ether extract
  10. customEvaporation to dryness
  11. customgave a residue which
  12. customwas triturated with dry ether
  13. customrecrystallised from an 8:2 mixture of propan-2-ol and ethanol

Sources & evidence

ORD record
ord-fcab1cc4338a4a9eaa00019e881c7769
Source dataset
uspto-grants-1986_12
Patent number
US04629727

Reaction notes

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