Morpholine → 1-(4-Chlorophenyl)-2-methyl-2-(morpholin-4-yl)propan-1-one

HRID 1380600Notes

Reaction equation

HRID 1380600 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([O:13]C)[C:10]([CH3:12])([CH3:11])O2)=[CH:4][CH:3]=1.[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:13])[C:10]([CH3:11])([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH3:12])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 122808342-(4-Chlorophenyl)-3,3-dimethyl-2-methoxyoxirane

Product 1

HCID 157024081-(4-Chlorophenyl)-2-methyl-2-(morpholin-4-yl)propan-1-one

Procedure

85.1 g (0.4 mol) of 2-(4-chlorophenyl)-3,3-dimethyl-2-methoxyoxirane and 139.4 g (1.6 mols) of morpholine are combined and warmed to reflux temperature. After 22 hours the mixture is cooled and morpholine is removed by distillation. The residue is taken up in ether, and the solution is extracted with dilute hydrochloric acid. The hydrochloric acid solution is rendered alkaline and extracted with ether. The ether solution is dried with Na2SO4 and concentrated. The residue is recrystallised from ethanol.

Workup

  1. temperaturewarmed
  2. temperatureto reflux temperature
  3. temperatureAfter 22 hours the mixture is cooled
  4. custommorpholine is removed by distillation
  5. extractionthe solution is extracted with dilute hydrochloric acid
  6. extractionextracted with ether
  7. dry with materialThe ether solution is dried with Na2SO4
  8. concentrationconcentrated
  9. customThe residue is recrystallised from ethanol

Sources & evidence

ORD record
ord-d7deaa3223c6449ea636abe9f7f0b94e
Source dataset
uspto-grants-1986_04
Patent number
US04582862

Reaction notes

Loading…