Morpholine → 1-(4-Fluorphenyl)-2-methyl-2-morpholino-1-propanone

HRID 376954Notes

Reaction equation

HRID 376954 reaction equation
[F: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>>[F: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 131131762-(4-Fluorophenyl)-2-methoxy-3,3-dimethyloxirane

Product 1

HCID 154053051-(4-Fluorphenyl)-2-methyl-2-morpholino-1-propanone

Conditions

Temperature
130 °C

Procedure

69.3 g (0.35 mol) of (4-fluorophenyl)-3,3-dimethyl-2-methoxyoxirane and 200 ml of dry morpholine are mixed and heated to reflux temperature (about 130° C.). After 26 h, the unreacted excess morpholine is distilled off. The residue is taken up in toluene and washed with water and saturated sodium chloride solution successively. The toluene solution is dried with MgSO4 and is concentrated. The residue, 88.1 g, crystallizes from ethanol with a melting point of 63-66° C.

Workup

  1. temperatureheated
  2. distillationthe unreacted excess morpholine is distilled off
  3. washwashed with water and saturated sodium chloride solution successively
  4. dry with materialThe toluene solution is dried with MgSO4
  5. concentrationis concentrated
  6. customThe residue, 88.1 g, crystallizes from ethanol with a melting point of 63-66° C.

Sources & evidence

ORD record
ord-e347a5ceb6504ef1b959459fc8ccbeb5
Source dataset
uspto-grants-2000_02
Patent number
US06022906

Reaction notes

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