Morpholine → 2-Methyl-2-morpholino-1-(4-piperidinophenyl)-propan-1-one

HRID 981756Notes

Reaction equation

HRID 981756 reaction equation
[CH3:1][C:2]1([CH3:19])O[C:3]1([O:17]C)[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:7][CH:6]=1.[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>>[CH3:19][C:2]([N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)([CH3:1])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:7][CH:6]=1)=[O:17]

Participants

3

Reactant 2

HCID 8083MorpholineHCID 198794483,3-Dimethyl-2-methoxy-2-(4-piperidinophenyl)-oxirane

Product 1

HCID 198794392-Methyl-2-morpholino-1-(4-piperidinophenyl)-propan-1-one

Conditions

Temperature
130 °C

Procedure

12.1 g (46.3 mmol) of 3,3-dimethyl-2-methoxy-2-(4-piperidinophenyl)-oxirane and 26.1 g (0.30 mol) of morpholine are added together, and the mixture is heated to the refluxing temperature (about 130° C.). After 6 hours the mixture is cooled down and the morpholine is distilled off under reduced pressure. The residue is taken up in toluene and 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 concentrated. The residue is recrystallised from methanol. Melting point 159°-162° C.

Workup

  1. temperatureAfter 6 hours the mixture is cooled down
  2. distillationthe morpholine is distilled off under reduced pressure
  3. extractionis extracted with dilute hydrochloric acid
  4. extractionis extracted with toluene
  5. dry with materialThe toluene solution is dried with K2CO3
  6. concentrationconcentrated
  7. customThe residue is recrystallised from methanol

Sources & evidence

ORD record
ord-8fef067ad98d4232add3817460531d19
Source dataset
uspto-grants-1991_02
Patent number
US04992547

Reaction notes

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