Tetrahydrofuran → (4-aminobenzyl)cyclohexylcarbamic Acid Benzyl Ester

HRID 348683Notes

Reaction equation

HRID 348683 reaction equation
[CH2:1]([O:8][C:9](=[O:27])[N:10]([CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.O.NN>CO.O.O.O.O.O.O.[Fe](Cl)(Cl)Cl>[CH2:1]([O:8][C:9](=[O:27])[N:10]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=1)[CH:21]1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 24654Hydrazine hydrate (1:1)HCID 66941326cyclohexyl(4-nitrobenzyl)carbamic Acid Benzyl Ester

Product 1

HCID 66941928(4-aminobenzyl)cyclohexylcarbamic Acid Benzyl EsterYield 101%

Reagents, catalysts & solvents 2

HCID 16211236Trichloroiron;hexahydrateCatalystHCID 887MethanolSolvent

Procedure

The compound (1.24 g) obtained in Example 87-1 was dissolved in methanol (12 ml) and THF (6.2 ml) and added with activated carbon (124 mg) and iron trichloride hexahydrate (12.4 mg), followed by thermal reflux for 0.5 hour. After standing to cool, the solution was added with hydrazine monohydrate (0.89 ml) and then subjected to thermal reflux for 3 hours. After completion of the reaction, the resultant was filtrated through Celite and the solvent was then distilled off. The residue was dissolved in chloroform and washed with water. The solution was dried with anhydrous magnesium sulfate. The solvent was distilled off, thereby obtaining the subject compound (1.15 g) as a yellow viscous liquid.

Workup

  1. temperatureby thermal reflux for 0.5 hour
  2. temperatureto cool
  3. temperaturethermal reflux for 3 hours
  4. customAfter completion of the reaction
  5. filtrationthe resultant was filtrated through Celite
  6. distillationthe solvent was then distilled off
  7. dissolutionThe residue was dissolved in chloroform
  8. washwashed with water
  9. dry with materialThe solution was dried with anhydrous magnesium sulfate
  10. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-f9057ea59b004ac58bd3935338a2af95
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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