Cyclohexene → Ethyl 3-amino-2-piperid-1-yl-5-trifluoromethylbenzoate

HRID 550353Notes

Reaction equation

HRID 550353 reaction equation
[N+:1]([C:4]1[C:5]([N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[C:6]([CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([O-])=O.C1CCCCC=1>C(O)C.[Pd]>[NH2:1][C:4]1[C:5]([N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[C:6]([CH:12]=[C:13]([C:15]([F:16])([F:17])[F:18])[CH:14]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 67201256Ethyl 3-nitro-2-piperid-1-yl-5-trifluoromethylbenzoate

Product 1

HCID 67202696Ethyl 3-amino-2-piperid-1-yl-5-trifluoromethylbenzoateYield 48%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of ethyl 3-nitro-2-piperid-1-yl-5-trifluoromethylbenzoate (4.9 g; 1 eq.) in ethanol (50 ml) are added cyclohexene (10.5 ml; 7.5 eq.) and 10% Pd/C (0.6 g), and the mixture is stirred at reflux for 5 hours. After removing the catalyst by filtration and concentrating to dryness, the pasty solid is purified by chromatography on silica (eluent: 4/1 pentane/ether). 2.15 g of ethyl 3-amino-2-piperid-1-yl-5-trifluoromethylbenzoate are obtained in the form of a reddish oil.

Workup

  1. temperatureat reflux for 5 hours
  2. customAfter removing the catalyst
  3. filtrationby filtration
  4. concentrationconcentrating to dryness
  5. customthe pasty solid is purified by chromatography on silica (eluent: 4/1 pentane/ether)

Sources & evidence

ORD record
ord-0e9ce815993248ccb93d2e962c6c956e
Source dataset
uspto-grants-2011_05
Patent number
US07947675B2

Reaction notes

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