Nitric Acid → HCID 13755073, compound

HRID 2309186Notes

Reaction equation

HRID 2309186 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[CH2:18][CH2:17][CH2:16][N:15]([C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])[CH2:14]2)=[CH:9][CH:8]=1>FC(F)(F)C(O)=O>[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[CH2:18][CH2:17][CH2:16][N:15]([C:19](=[O:24])[C:20]([F:21])([F:22])[F:23])[CH2:14]2)=[CH:9][C:8]=1[N+:1]([O-:4])=[O:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 13755072HCID 13755072, compound

Product 1

HCID 13755073HCID 13755073, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

2.24 ml of fuming nitric acid were added dropwise with stirring to 14.3 g of the product of Step C in 50 ml of trifluoroacetic acid at 0° C. The temperature was allowed to return to ambient and the mixture was stirred for 1 hour. After pouring the mixture on ice, extracting with methylene chloride, washing with water, drying, evaporating to dryness under reduced pressure, and purifying by chromatography over silica (eluent benzene - ethyl acetate 9-1), 12.3 g of 3-(4-methoxy-3-nitrophenyl)-1-(trifluoroacetyl)-piperidine were obtained which after crystallization from isopropyl ether melted at 96° C.

Workup

  1. additionAfter pouring the mixture on ice
  2. extractionextracting with methylene chloride
  3. washwashing with water
  4. customdrying
  5. customevaporating to dryness under reduced pressure
  6. custompurifying by chromatography over silica (eluent benzene - ethyl acetate 9-1)

Sources & evidence

ORD record
ord-24a4b6c0ac344eaebf040a5881c726c3
Source dataset
uspto-grants-1987_09
Patent number
US04694011

Reaction notes

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