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

HRID 704749Notes

Reaction equation

HRID 704749 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.N[N:25]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.C[N:33](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:33]([CH:26]3[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][NH:25]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 221981-AminohomopiperidineHCID 143002712-(4-Fluorophenyl)-5-methyl-1-phenylhexane-1,4-dione

Product 1

HCID 572057433-(4-Fluorophenyl)-1-hexahydroazepinyl-5-isopropyl-2-phenyl-pyrrole

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.7 ml of conc. hydrochloric acid are added to 5 g (16.7 mmol) of the compound from Example 2 and 5.7 g (50.1 mmol) of N-amino-hexahydroazepine in 100 ml of toluene AR and 80 ml of dimethylformamide and the mixture is boiled in a water separator for 24 hours. 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 1:9).

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 1:9)

Sources & evidence

ORD record
ord-5c4a30a59ebc470a8bb4038ba1edcf5a
Source dataset
uspto-grants-1991_01
Patent number
US04988711

Reaction notes

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