Piperidine → 2-Methyl-1-(4-(piperidin-1-yl)phenyl)propan-1-one

HRID 981753Notes

Reaction equation

HRID 981753 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:12])[CH:9]([CH3:11])[CH3:10])=[CH:4][CH:3]=1.C(Cl)(=O)C(C)C.FC1C=CC=CC=1.[NH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:10][CH:9]([CH3:11])[C:8]([C:5]1[CH:6]=[CH:7][C:2]([N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)=[CH:3][CH:4]=1)=[O:12]

Participants

7

Reactant 5

HCID 8082PiperidineHCID 10008FluorobenzeneHCID 11430Potassium CarbonateHCID 62325Isobutyryl chlorideHCID 27828291-(4-Fluorophenyl)-2-methylpropan-1-one

Product 1

HCID 212571912-Methyl-1-(4-(piperidin-1-yl)phenyl)propan-1-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

49.86 (0.30 mol) of 1-(4-fluorophenyl)-2-methylpropan-1-one, prepared by a Friedel-Crafts reaction from isobutyryl chloride with fluorobenzene analogously to European Patent Application No. 3,002, and 25.5 g (0.30 mol) of piperidine are dissolved in 120 ml of dimethyl sulfoxide, and the solution is heated to 110° C. together with 41.5 g (0.30 mol) of potassium carbonate. After 16 hours of stirring at 110° C. the suspension is cooled down and is poured onto an ice-water mixture. The crystals are filtered off, are washed with water and are recrystallised from hexane.

Workup

  1. temperatureis cooled down
  2. filtrationThe crystals are filtered off
  3. washare washed with water
  4. customare recrystallised from hexane

Sources & evidence

ORD record
ord-60e72f52f6ba490586c066d66c9515a9
Source dataset
uspto-grants-1991_02
Patent number
US04992547

Reaction notes

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