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

HRID 1885644Notes

Reaction equation

HRID 1885644 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

29.43 g (0.15 mol) of 2-(4-fluorophenyl)-3,3-dimethyl-2-methoxyoxirane and 52.3 g (0.60 mol) of morpholine are brought together, and the mixture is heated to reflux temperature (about 130° C.). After 23 hours the excess morpholine is distilled off. The residue is taken up with toluene, and the mixture is extracted with dilute hydrochloric acid. The hydrochloric acid solution is rendered alkaline and is extracted with toluene. The toluene solution is dried with K2CO3 and is concentrated. The residue, 34.0 g, crystallises out from ethyl acetate with a melting point of 63°-66° C.

Workup

  1. temperaturethe mixture is heated
  2. distillationAfter 23 hours the excess morpholine is distilled off
  3. extractionthe mixture is extracted with dilute hydrochloric acid
  4. extractionis extracted with toluene
  5. dry with materialThe toluene solution is dried with K2CO3
  6. concentrationis concentrated
  7. customThe residue, 34.0 g, crystallises out from ethyl acetate with a melting point of 63°-66° C.

Sources & evidence

ORD record
ord-ecc0b4b4a4444506a5322dc30a8772cb
Source dataset
uspto-grants-1992_09
Patent number
US05145885

Reaction notes

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