Azane;hydrate → HCID 14576908, compound

HRID 1904627Notes

Reaction equation

HRID 1904627 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:15]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=3)[CH2:14][CH2:13][CH2:12][C:11]2=[O:24])=[CH:6][CH:5]=1)([O-])=O.O.N>CO.[Cl-].[Cl-].[Cl-].[Ti+3]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:15]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=3)[CH2:14][CH2:13][CH2:12][C:11]2=[O:24])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 12896473Azane;hydrateHCID 14576878HCID 14576878, compound

Product 1

HCID 14576908HCID 14576908, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 10313229titanium(III) trichlorideCatalystHCID 887MethanolSolvent

Procedure

A solution of 6.5 g of 1-(4-nitrophenyl)-6-(3,4-dichlorophenyl)-2-piperidone in 180 ml of methanol was cooled to 4° C., and then 110 g of 25% titanium trichloride was added dropwise to the solution. After stirring at 18° to 20° C. for 40 minutes, the reaction mixture was poured into cold ammonia water and the precipitates were filtered off. The filtrate was extracted with chloroform. On the other hand, the precipitate obtained above was throughly washed with chloroform. The chloroform layer was combined with the former, washed with water, dried, and concentrated. The residue was recrystallized from ethanol to give 4.59 g of 1-(4-aminophenyl)-6-(3,4-dichlorophenyl)-2-piperidone as colorless prisms.

Workup

  1. filtrationthe precipitates were filtered off
  2. extractionThe filtrate was extracted with chloroform
  3. customOn the other hand, the precipitate obtained
  4. washabove was throughly washed with chloroform
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-93bf49fe32ec4e388042e99a648a2856
Source dataset
uspto-grants-1989_06
Patent number
US04839360

Reaction notes

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