HCID 86670935, compound → 4-(4-Nitrobenzylidene)piperidine

HRID 515278Notes

Reaction equation

HRID 515278 reaction equation
[N+:1]([C:4]1[CH:23]=[CH:22][C:7]([CH:8]=[C:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]>ClCCl.FC(F)(F)C(O)=O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:8]=[C:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]2)=[CH:22][CH:23]=1)([O-:3])=[O:2]

Participants

3

Reactant 1

HCID 86670935HCID 86670935, compound

Product 1

HCID 671941644-(4-Nitrobenzylidene)piperidineYield 75.9%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

tert-Butyl 4-(4-nitrobenzylidene)piperidine-1-carboxylate (31.4 mmol, 10 g) was stirred in a mixture of dichloromethane/trifluoroacetic acid for 3 hours. The reaction was concentrated under reduced pressure and water was added. Solid sodium hydrogen carbonate was added portionwise until no further gas was evolved. The aqueous mixture was extracted with ethyl acetate. The organic phase was dried (magnesium sulfate), filtered and concentrated under reduced pressure to give the title compound (5.2 g). MS (ESI) m/z 219.1 [M+H]+

Workup

  1. concentrationThe reaction was concentrated under reduced pressure and water
  2. additionwas added
  3. additionSolid sodium hydrogen carbonate was added portionwise until no further gas
  4. extractionThe aqueous mixture was extracted with ethyl acetate
  5. dry with materialThe organic phase was dried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2b9e6764ad3f4d2493a39c833fe9d1bd
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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