Hydrochloric Acid → 3-(4-Fluorophenyl)-5-isopropyl-1-(4-methylpiperidino)-2-phenyl-pyrrole

HRID 704750

Reaction equation

HRID 704750 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH2:18][C:19](=O)[CH:20]([CH3:22])[CH3:21])[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=O)=[CH:5][CH:4]=1.[NH2:24][N:25]1[CH2:30][CH2:29][CH:28]([CH3:31])[CH2:27][CH2:26]1.CN(C)C=O>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:18]=[C:19]([CH:20]([CH3:22])[CH3:21])[N:24]([N:25]3[CH2:30][CH2:29][CH:28]([CH3:31])[CH2:27][CH2:26]3)[C:10]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:5][CH:4]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 37335874-Methylpiperidin-1-amineHCID 143002712-(4-Fluorophenyl)-5-methyl-1-phenylhexane-1,4-dione

Product 1

HCID 145787713-(4-Fluorophenyl)-5-isopropyl-1-(4-methylpiperidino)-2-phenyl-pyrrole

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

3.4 ml of conc. hydrochloric acid are added to 10.1 g (34 mmol) of the compound from Example 2 and 11.6 g (102 mmol) of N-amino-4-methyl-piperidine in 100 ml of toluene AR and 50 ml of dimethylformamide and the mixture is boiled for 24 hours in a water separator. The mixture is cooled, diluted using 200 ml of ethyl acetate and extracted three times using 1N hydrochloric acid and twice using saturated sodium hydrogen carbonate solution. The organic phase is dried over magnesium sulphate and concentrated in vacuo, and the residue is chromatographed on a column (silica gel 70-230 mesh, using ethyl acetate/petroleum ether 5:95).

Workup

  1. temperatureThe mixture is cooled
  2. additiondiluted
  3. extractionextracted three times
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. customthe residue is chromatographed on a column (silica gel 70-230 mesh, using ethyl acetate/petroleum ether 5:95)

Sources & evidence

ORD record
ord-ded4a07d12c349e18f01b4b42b5ff57f
Source dataset
uspto-grants-1991_01
Patent number
US04988711

Linked notes

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