HCID 57196678, compound → HCID 57196809, compound

HRID 2198965Notes

Reaction equation

HRID 2198965 reaction equation
ClC(Cl)(Cl)COC([CH:7]1[CH:12]2[CH2:13][CH2:14][N:8]1[CH2:9][C:10](=[N:15][N:16]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:11]2)=O>C(O)(=O)C.[Zn]>[C:23]1([N:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:15]=[C:10]2[CH2:9][N:8]3[CH2:14][CH2:13][CH:12]([CH2:7]3)[CH2:11]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 1

HCID 57196678HCID 57196678, compound

Product 1

HCID 57196809HCID 57196809, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Zinc dust (90.0 g) is added in small portions to a well-stirred mixture of 5-(2,2-diphenylhydrazono)-1,3-ethanopiperidine-2-carboxylic acid-2,2,2-trichloroethylester in 300 ml of glacial acetic acid, maintaining the reaction temperature between 40° C.-60° C. with external cooling when necessary. Upon completion of the addition, stirring is continued at ambient temperature for 45 minutes. The insoluble material is filtered and the resulting clear yellow filtrate contains the desired product and can be used in the succeeding Fisher-Indole synthesis procedures.

Workup

  1. temperaturemaintaining the reaction temperature between 40° C.-60° C.
  2. temperaturewith external cooling when necessary
  3. additionUpon completion of the addition
  4. filtrationThe insoluble material is filtered
  5. customcan be used in the succeeding Fisher-Indole synthesis procedures

Sources & evidence

ORD record
ord-638e97a66e324e048aea81b73820d582
Source dataset
uspto-grants-1982_11
Patent number
US04360673

Reaction notes

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