ST50251142 → HCID 10684164, compound

HRID 1729652Notes

Reaction equation

HRID 1729652 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][C:17]=1[N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8])([O-])=O>[Fe].C(O)(=O)C>[NH2:1][C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][C:17]=1[N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8]

Participants

4

Reactant 1

HCID 626066ST50251142

Product 1

HCID 10684164HCID 10684164, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×

Procedure

A solution of 6.5 g. of 3-nitro-4-piperidino-benzophenone in 80 ml. of glacial acetic acid is added dropwise into a well stirred mixture of 5.3 g. of iron powder and 25 ml. of glacial acetic acid. The reaction mixture is kept at 80° to 90° C for about 2 hours. During this period the reaction takes place completely. The heterogeneous reaction mixture is cooled, filtered, and the filtrate is evaporated under reduced pressure. The residue is dissolved in water and the solution is rendered alkaline. This mixture is extracted with benzene, the benzene solution is washed with water until neutral, dried over anhydrous magnesium sulphate, filtered through a column filled with silica gel, and evaporated under reduced pressure. This way 4.5 g. of a solid, crystalline substance are obtained. The physical constants of the product are the same as given in Example 10.

Workup

  1. additionmixture of 5.3 g
  2. waitDuring this period the reaction takes
  3. temperatureThe heterogeneous reaction mixture is cooled
  4. filtrationfiltered
  5. customthe filtrate is evaporated under reduced pressure
  6. dissolutionThe residue is dissolved in water
  7. extractionThis mixture is extracted with benzene
  8. washthe benzene solution is washed with water until neutral,
  9. dry with materialdried over anhydrous magnesium sulphate
  10. filtrationfiltered through a column
  11. additionfilled with silica gel
  12. customevaporated under reduced pressure
  13. customof a solid, crystalline substance are obtained

Sources & evidence

ORD record
ord-6fc46fee3f8e45efa2142de982c2aee0
Source dataset
uspto-grants-1976_11
Patent number
US03989701

Reaction notes

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